Infrared-absorptive compound and optical recording medium making use of the same

ABSTRACT

An infrared-absorptive compound is disclosed which has the structure represented by the following formula (I) or (II) ##STR1## Also, an optical recording medium having a recording layer containing the infrared-absorptive compound is disclosed.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a novel infrared-absorptive compoundand an optical recording medium making use of the infrared-absorptivecompound.

2. Related Background Art

Generally, information can be recorded on optical recording mediums suchas optical disks and optical cards by forming optically detectableminute pits (with size of, for example, about 1 μm) so arranged as toprovide a spiral, concentric or linear track or tracks on a recordinglayer formed on a substrate of the recording medium, thereby making itpossible to store information at a high density.

As describe, for example, in "Review and Analysis of Optical RecordingMedia", Optical Engineering, Vol. 15, No. 2, March-April 1976, p. 99ff., a known optical recording method comprises applying a light beamsuch as a laser beam to the recording layer of an optical recordingmedium so as to generate deformation or pits on the recording layer. Inother known methods, the application of such a light beam causes thegeneration of bubbles, phase changes, discoloration, discolorization orthe like.

Various materials have been proposed for the recording layer of suchoptical recording mediums. Examples of the materials include inorganicmaterials such as a metal film comprised of an aluminum deposit film orthe like, a bismuth film, a tellurium oxide film and a chalcogenite typenon-crystalline glass film. Such thin films are commonly sensitive tolight having a wavelength of approximately 350 to 800 nm and exhibit ahigh reflectance to laser beams. One disadvantage of these films is thatthey provide a rather poor laser beam ultilization factor. Moreover,such inorganic material thin films are usually formed as recordinglayers by sputtering or the like. Such a film forming method, however,requires a production line equipped with a vacuum system, so that theseinorganic material thin films are involved in a higher production cost.

In view of the above problems, optical recording mediums using coloringmatter whose optical properties can be changed by the energy of lighthaving a relatively long wavelength (for example, 780 nm or more) arebeing extensively studied. Optical recording mediums using such organiccoloring matter are effective in that they allow the formation-of pitsby a semiconductor laser having an oscillation wavelength of around 780nm or 830 nm. Organic coloring matter also allows film formation by wetcoating and can be handled with ease, making it possible to readilymass-produce recording mediums at less equipment cost.

The optical recording mediums making use of organic coloring matter inthe recording layer, however, commonly have a poor light-resistancestability. For example, when such optical recording mediums are leftunder natural light or repeatedly irradiated with reproducing light,there has been the problem that the recording-reproducing performance ofthe optical recording mediums is lowered. To cope with such a problem, amethod in which a nickel chelate complex serving as a singlet oxygenquencher is added to a recording layer is known in the art (for example,Japanese Patent Applications Laid-open No. 63-1594, No. 63-9576, No.63-31792, No. 63-67187, No. 63-78794 and No. 63-82789).

The nickel chelate complex compound, however, has so poor a solventsolubility that it has been difficult for it to be added in an amountlarge enough to well improve the light-resistance of the recording layerwhen the recording layer is formed by wet coating.

In the meantime, the present applicants have disclosed in U.S. Pat. Nos.4,656,121 and 4,923,390 a technique in which an infrared-absorptivecompound such as a triallylamine type aminium salt compound or diimoniumsalt compound is added to the recording layer in order to improvelight-resistance stability of the organic coloring matter recordinglayer. The aminium salt compound and diimonium salt compound have abetter solvent solubility than the nickel chelate complex and areeffective for well improving light-resistance stability of the recordinglayer.

Incidentally, temperatures inside apparatus tend to rise asrecording-reproducing apparatus for optical recording mediums have beenmade small-sized in recent years. In addition, optical recording mediumssuch as optical cards, of the type they are carried by personal users,are not necessarily used only in offices well air-conditioned. Forexample, even a condition in which they are left for a long time in anenvironment of high temperature as in rooms of automobiles must be takeninto consideration. Thus, there is a demand for optical recordingmediums having much better storage stability in the environment of hightemperature. With such a demand, the aminium salt compound or diimoniumsalt compound itself which is added to the recording layer in order toimprove light-resistance stability as stated above is sought to havemuch more improved heat-resistance while retaining the solventsolubility.

SUMMARY OF THE INVENTION

The present invention was made taking account of the above problems. Anobject of the present invention is to provide an infrared-absorptivecompound having a superior solvent solubility and at the same timehaving a superior heat resistance.

Another object of the present invention is to provide an opticalrecording medium comprising an organic coloring matter having a superiorlight-resistance stability and also having a superior storage stabilityin an environment of high temperature.

The infrared-absorptive compound of the present invention ischaracterized by having the structure represented by the followingformula (I) or (IT). ##STR2## In formulas (I) and (II), R₀ to R₇ eachrepresent (a) a hydrogen atom or a monovalent organic residual group, atleast one of R₀ to R₇ being a monovalent organic residual group having afluorine atom, or (b) a group of atoms necessary for at least one ofcombinations R₀ and R₁, R₂ and R₃, R₄ and R₅ and R₆ and R₇ to formtogether with a nitrogen atom a substituted or unsubstituted 5-memberedring having a fluorine atom, a substituted or unsubstituted 6-memberedring having a fluorine atom or a substituted or unsubstituted 7-memberedring having a fluorine atom, other combinations each being a hydrogenatom or a monovalent organic residual group; and X.sup.⊖ represents ananionic residual group.

In formula (I), "A" represents ##STR3## In formula (II), "B" represents##STR4## wherein n represents an integer of 1 or 2.

The infrared-absorptive compound of the present invention is alsocharacterized by having the structure represented by the followingformula (III) or (IV). ##STR5## In formulas (III) and (IV), R'₁ to R'₁₆each represent a hydrogen atom or a monovalent organic residual group,or a group of atoms necessary for any combination of R'_(q) and R'_(q+1)to form a substituted or unsubstituted 5-membered ring, a substituted orunsubstituted 6-membered ring or a substituted or unsubstituted7-membered ring, wherein q is 1, 3, 5, 7, 9, 11 or 13; and X.sup.⊖represents an anionic residual group.

The infrared-absorptive compound of the present invention is alsocharacterized by having the structure represented by the followingformula (V) or (VI). ##STR6## In formulas (V) and (VI), Z represents##STR7## and R"₁ to R"₉ each represent a hydrogen atom or a monovalentorganic residual group, or a group of atoms necessary for anycombination of R"_(r) and R"_(r+1) to form a substituted orunsubstituted 5-membered ring, a substituted or unsubstituted 6-memberedring or a substituted or unsubstituted 7-membered ring, wherein r is 1,3, 5 or 7; and X.sup.⊖ represents an anionic residual group.

The optical recording medium of the present invention comprises arecording layer containing an infrared-absorptive compound representedby the following formula (I) or (II). ##STR8## In formulas (I) and (II),R₀ to R₇ each represent (a) a hydrogen atom or a monovalent organicresidual group, at least one of R₀ to R₇ being a monovalent organicresidual group having a fluorine atom, or (b) a group of atoms necessaryfor at least one of combinations R₀ and R₁, R₂ and R₃, R₄ and R₅ and R₆and R₇ to form together with a nitrogen atom a substituted orunsubstituted 5-membered ring having a fluorine atom, a substituted orunsubstituted 6-membered ring having a fluorine atom or a substituted orunsubstituted 7-membered ring having a fluorine atom, other combinationseach being a hydrogen atom or a monovalent organic residual group; andX.sup.⊖ represents an anionic residual group.

In formula (I), "A" represents ##STR9## In formula (II), "B" represents##STR10## wherein n represents an integer of 1 or 2.

The optical recording medium of the present invention also comprises arecording layer containing an infrared-absorptive compound representedby the following formula (III) or (IV). ##STR11## In formulas (III) and(IV), R'₁ to R'₁₆ each represent a hydrogen atom or a monovalent organicresidual group, or a group of atoms necessary for any combination ofR'_(q) and R'_(q+1) to form a substituted or unsubstituted 5-memberedring, a substituted or unsubstituted 6-membered ring or a substituted orunsubstituted 7-membered ring, wherein q is 1, 3, 5, 7, 9, 11 or 13; andX.sup.⊖ represents an anionic residual group.

The optical recording medium of the present invention also comprises arecording layer containing an infrared-absorptive compound representedby the following formula (V) or (VI). ##STR12## In formulas (V) and(VI), Z represents ##STR13## and R"₁ to R"₉ each represent a hydrogenatom or a monovalent organic residual group, or a group of atomsnecessary for any combination of R"_(r) and R"_(r+1) to form asubstituted or unsubstituted 5-membered ring, a substituted orunsubstituted 6-membered ring or a substituted or unsubstituted7-membered ring, wherein r is 1, 3, 5 or 7; and X.sup.⊖ represents ananionic residual group.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a cross-sectional illustration of an embodiment of the opticalrecording medium according to the present invention.

FIG. 2 is a cross-sectional illustration of another embodiment of theoptical recording medium according to the present invention.

FIG. 3 is a cross-sectional illustration of still another embodiment ofthe optical recording medium according to the present invention.

FIG. 4 is a cross-sectional illustration of still another embodiment ofthe optical recording medium according to the present invention.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The present invention will be described below in detail.

The infrared-absorptive compound according to a first embodiment of thepresent invention is a compound represented by the following formula (I)or (II). ##STR14## In formulas (I) and (II), R₀ to R₇ each represent ahydrogen atom or a monovalent organic residual group, and in the presentinvention, at least one of the substituents R₀ to R₇ is preferably amonovalent organic residual group having a fluorine atom (hereinafterabridged "R_(F) "). The compound wherein at least one of R₀ to R₇ isR_(F) can bring about a more improvement in heat resistance than theconventional aminium salt compounds or diimonium salt compounds.

In the present invention, the R_(F) preferably used in R₀ to R₇ areexemplified by a substituted or unsubstituted alkyl group having afluorine atom, a substituted or unsubstituted alkenyl group having afluorine atom, a substituted or unsubstituted aralkyl group having afluorine atom and a substituted or unsubstituted aryl group having afluorine atom.

In the present invention, for example, what is meant by the"unsubstituted aryl group having a fluorine atom" in the description forthe R_(F) is that hydrogen atom(s) is/are not substituted with otherelement(s) or organic residual group(s) except that one or two or morehydrogen atom(s) in the phenyl group is/are substituted with a fluorineatom or atoms, and what is meant by the "substituted aryl group having afluorine atom" is that one or two or more hydrogen atom(s) in the phenylgroup is/are substituted with a fluorine atom or atoms and also one ortwo or more hydrogen atom(s) in the phenyl group is/are substituted withother element(s) or monovalent organic residual group(s) or that one ortwo or more hydrogen atom(s) in the phenyl group is/are substituted witha monovalent organic residual group or groups having a fluorine atom.

The R_(F) in the present invention will be described below in greaterdetail. For example, the unsubstituted alkyl group having a fluorineatom may include those exemplified by a fluoromethyl group, adifluoromethyl group, a trifluoromethyl group, a 1-fluoroethyl group, a2-fluoroethyl group, a 1,1-difluoroethyl group, a 1,2-difluoroethylgroup, a 2,2-difluoroethyl group, a 1,1,1-trifluoroethyl group, a1,1,2-trifluoroethyl group, a 1,2,2-trifluoroethyl group, a1,1,2,2-tetrafluoroethyl group, a 1,1,1,2-tetrafluoroethyl group, apentafluoroethyl group, a 1-fluoropropyl group, a 2-fluoropropyl group,a 3-fluoropropyl group, a 1,1-difluoropropyl group, a 1,2-difluoropropylgroup, a 1,3-difluoropropyl group, a 2,2-difluoropropyl group, a2,3-difluoropropyl group, a 3,3-difluoropropyl group, a1,1,2-trifluoropropyl group, a 1,1,3-trifluoropropyl group, a1,2,2-trifluoropropyl group, a 1,2,3-trifluoropropyl group, a1,3,3-trifluoropropyl group, a 2,2,3-trifluoropropyl group, a3,3,3-trifluoropropyl group, a 1,1,2,2-tetrafluoropropyl group, a1,1,3,3-tetrafluoropropyl group, a 1,1,2,3-tetrafluoropropyl group, a1,2,2,3-tetrafluoropropyl group, a 1,2,3,3-tetrafluoropropyl group, a2,2,3,3-tetrafluoropropyl group, a 1,3,3,3-tetrafluoropropyl group, a2,3,3,3-tetrafluoropropyl group, a 1,1,2,2,3-pentafluoropropyl group, a1,1,2,3,3-pentafluoropropyl group, a 1,1,3,3,3-pentafluoropropyl group,a 1,2,2,3,3-pentafluoropropyl group, a 1,2,3,3,3-pentafluoropropylgroup, a 2,2,3,3,3-pentafluoropropyl group, a1,1,2,2,3,3-hexafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropylgroup, a 1,2,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group,a 1,1,1,3,3,3-hexafluoro-2-propyl group, a heptafluoro-2-propyl group, a2,2-difluorobutyl group, a 2,2,3,3-tetrafluorobutyl group, a4,4,4-trifluorobutyl group, a 3,3,4,4,4-pentafluorobutyl group, a2,2,4,4,4-pentafluorobutyl group, a 2,2,3,4,4,4-hexafluorobutyl group, a1,2,3,4-tetrafluorobutyl group, a nonafluorobutyl group, a2,2,3,3,4,4,4-heptafluorobutyl group, a1,1,3,3,4,4,4-heptafluoro-2-butyl group, a t-nonafluorobutyl group, a5,5,5-trifluoropentyl group, a 4,4,5,5,5-pentafluoropentyl group, a3,3,5,5,5-pentafluoropentyl group, a 3,3,4,4-tetrafluoropentyl group, a1,2,3,4,5-pentafluoropentyl group, a 2,2,3,3,4,4,5,5-octafluoro-1-pentylgroup, a 1,1,2,2,3,3,4,4-octafluoropentyl group, a 6,6,6-trifluorohexylgroup, a 6,6,7,7,7-pentafluoropentyl group, a 8,8,8-trifluorooctyl groupand a 5,5,6,6,7,7,8,8-octafluorooctyl group.

Other alkyl group having a fluorine atom, for example, the substitutedalkyl group having a fluorine atom may include fluorine-containinghydroxylalkyl groups such as a 2-hydroxy-2-fluoroethyl group, a2-hydroxy-1,1-difluoroethyl group and a 3-hydroxy-2,2-difluoropropylgroup, fluorine-containing acetoxylalkyl groups such as a2-acetoxy-2-fluoroethyl group, a 2-acetoxy-2,2-difluoroethyl group and a3-acetoxy-2,2,3,3-tetrafluoropropyl group, fluorine-containingcarboxylalkyl groups such as a 2-carboxy-1,2-difluoroethyl group, a3-carboxy-3-fluoropropyl group and a 4-carboxy-2,2-difluorobutyl group,and fluorine-containing alkoxylalkyl groups such as atrifluoromethoxymethy1 group, a trifluoromethoxyethyl group, atrifluoromethoxy-2-difluoroethyl group, a difluoromethoxyethy1 group, a2-trifluoroethoxy-2'-difluoroethyl group, a trifluoromethoxy-n-propylgroup, a pentafluoroethoxyethyl group, a pentafluoroethoxypropyl group,a methoxy-3,3-difluoropropyl group and a trifluoromethoxyoctyl group.

The unsubstituted alkenyl group having a fluorine atom may include thoseexemplified by a trifluoroethylene group, a 2,2-difluoroethylene group,a pentafluoropropenyl group and a heptafluorobutenyl group. Thesubstituted alkenyl group having a fluorine atom may include thoseexemplified by a 2-hydroxy-3,3-difluoropropenyl group.

The unsubstituted aralkyl group having a fluorine atom may include thoseexemplified by a p-fluorobenzy1 group, a m-fluorobenzy1 group, apentafluorobenzyl group, a p-trifluoromethylbenzyl group, a1-(pentafluorophenyl)ethyl group and 3-(pentafluorophenyl)propyl group.

The substituted aralkyl group having a fluorine atom may include thoseexemplified by a 4-hydroxy-3-fluorobenzyl group.

The unsubstituted aryl group having a fluorine atom may include ap-fluorophenyl group and a pentafluorophenyl group. The substituted arylgroup having a fluorine atom may include a p-trifluoromethylphenyl groupand a 3,5-bis(trifluoromethyl)phenyl group.

In view of the improvement in heat resistance of the optical recordingmedium, it is preferable in the present invention that at least one ofR₀ to R₇ in the organic coloring matter represented by formula (I) isthe R_(F) as previously described. In particular, a polymethine dyewherein at least one of R₀ and R₁ and at least one of R₄ and R₅ are theR_(F) or all of R₀ to R₇ are the R_(F) can bring about the improvementin heat resistance of the optical recording medium. This is a preferredembodiment.

In the present invention, among R₀ to R₇, the remaining substituent(s)other than those having been taken by the R_(F) may be a hydrogen atomor atoms or a monovalent organic residual group or groups other than theR_(F). In this instance, the monovalent organic residual group otherthan the R_(F) may include alkyl groups as exemplified by a methylgroup, an ethyl group, a n-propyl group, an iso-propyl group, a n-butylgroup, an iso-butyl group, a t-butyl group, a n-amyl group, a t-amylgroup, a n-hexyl group, a n-octyl group and a t-octyl group. Other alkylgroups as exemplified by substituted alkyl groups may include, forexample, hydroxyalkyl groups such as a 2-hydroxyethyl group, a3-hydroxypropyl group and a 4-hydroxybutyl group, acetoxyalkyl groupssuch as a 2-acetoxyethyl group and a 2-acetoxypropyl group, carboxyalkylgroups such as a carboxymethyl group, a 2-carboxyethyl group and a3-carboxypropyl group, and alkoxyalkyl groups such as a methoxymethylgroup, a methoxyethyl group, a methoxypropyl group, a methoxybutylgroup, an ethoxymethyl group, an ethoxyethyl group, an ethoxypropylgroup, an ethoxybutyl group and a propoxymethyl group; aralkyl groups asexemplified by a benzyl group, a p-chlorobenzyl group, a p-methylbenzylgroup, a 2-phenylmethyl group, a 2-phenylpropyl group, a 3-phenylpropylgroup, an α-naphthylmethyl group and a β-naphthylethyl group; and alsosubstituted or unsubstituted aryl groups as exemplified by a phenylgroup, a naphthyl group, a tolyl group, a xylyl group, a methoxyphenylgroup, a dimethoxyphenyl group, a trimethoxyphenyl group, anethoxyphenyl group, a dimethylaminophenyl group, a diethylaminophenylgroup, a dipropylaminophenyl group, a dibenzylaminophenyl group, adiphenylaminophenyl group and a ditolylaminophenyl group.

In the present invention, in the case when at least two or more of thesubstituents R₀ to R₇ are R_(F) 's, the R_(F) 's may be the same or maybe different from one another.

Of the various R_(F) 's described above in the present invention, thesubstituted or unsubstituted alkyl groups or alkoxyalkyl groups having afluorine atom are preferable organic residual groups in view ofachievement of both the effects, i.e., improvements in heat resistanceand solubility in organic solvents, of the compound. In this instance,the alkyl group may preferably have 1 to 8, and particularly 1 to 5,carbon atoms.

In formulas (I) and (II) described above, among R₀ to R₇, at least oneof combinations R₀ and R₁, R₂ and R₃, R₄ and R₅ and R₆ and R₇ may formtogether with a nitrogen atom a substituted or unsubstituted 5-memberedring having a fluorine atom, a substituted or unsubstituted 6-memberedring having a fluorine atom or a substituted or unsubstituted 7-memberedring having a fluorine atom. Such a compound can also bring about a moreimprovement in heat resistance than the conventional aminium saltcompounds or diimonium salt compounds.

Here, the 5-membered ring may include, for example, a pyrrolidine ring,the 6-membered ring may include a piperidine ring, a morpholine ring anda tetrahydropyridine group, and the 7-membered ring may include acylcohexylamine ring as represented by the following formula (VII).##STR15## Here, among R₀ to R₇, the remaining substituent(s) other thanthose forming no heterocyclic ring may be a hydrogen atom or amonovalent organic residual group including the R_(F), and two or moreof combinations R₀ and R₁, R₂ and R₃, R₄ and R₅ end R₆ and R₇ may formthe above 5-membered, 6-membered or 7-membered ring having a fluorineatom. In this instance, each ring may be the same or different.

In the case when R₀ to R₇ form the above heterocyclic rings, it ispreferable for them to have the structure of any of the followingformulas (VIII)-(1) to (VIII)-(4), in view of the improvement of heatresistance of the compound and solubility in organic solvents. ##STR16##The heat resistance and solubility in organic solvents, of the compoundof formula (I) or (II) can be much more improved when all thecombinations R₀ and R₁, R₂ and R₃, R₄ and R₅ and R₆ and R₇ are made tohave the structure of any of the above formulas (VIII)-(1) to(VIII)-(4).

X.sup.⊖ represents an anion such as a chloride ion, a bromide ion, aniodide ion, a perchlorate ion, a nitrate ion, a benzenesulfonate ion, ap-toluenesulfonate ion, a methyl sulfate ion, an ethyl sulfate ion, apropyl sulfate ion, a tetrafluoroborate ion, a tetraphenylborate ion, ahexafluorophosphate ion, a benzenesulfinate ion, an acetate ion, atrifluoroacetate ion, a propionacetate ion, a benzoate ion, an oxalateion, a succinate ion, a malonate ion, an oleate ion, a stearate ion, acitrate ion, a monohydrogen diphosphate ion, a dihydrogen monophosphateion, a pentachlorostannate ion, a chlorosulfonate ion, a fluorosulfonateion, a trifluoromethane sulfonate ion, a hexafluoroarsenate ion, ahexafluoroantimonate ion, a molybdate ion, a tungstate ion, a titanateion or a zirconate ion.

Examples of the infrared-absorptive compounds of formulas (I) and (II)according to the present invention are shown below. In the presentinvention, examples are by no means limited to these.

The following exemplary compounds (I)-(A)-(1) to (II)-(D)-(14) ape setout in the manner simplified as follows:

For example, in the infrared-absorptive compounds of formulas (I) and(II), compounds having the following structures (A), (B) and (C) arerespectively indicated as shown below.

    __________________________________________________________________________    (A)                                                                               ##STR17##                                                                 (B)                                                                               ##STR18##                                                                 (C)                                                                               ##STR19##                                                                 Compound No.                                                                           A(B)      X   (R.sub.0, R.sub.1)(R.sub.2, R.sub.3)(R.sub.4,                                 R.sub.5)(R.sub.6, R.sub.7)                             __________________________________________________________________________    (A)                                                                                     ##STR20##                                                                              ClO.sub.4                                                                         (CH.sub.2 CF.sub.3, CH.sub.2 CF.sub.3).sub.4           (B)                                                                                     ##STR21##                                                                              NO.sub.2                                                                           ##STR22##                                             (C)                                                                                     ##STR23##                                                                              AsF.sub.6                                                                         (C.sub.3 F.sub.7, C.sub.3 F.sub.7)(C.sub.3                                    H.sub.7, C.sub.3 H.sub.7).sub.3                        __________________________________________________________________________

    __________________________________________________________________________    Compound                                                                      No.    A              X           (R.sub.0 R.sub.1) (R.sub.2 R.sub.3)                                           (R.sub.4 R.sub.5) (R.sub.6 R.sub.7)         __________________________________________________________________________    [I]-(A)-(1)                                                                           ##STR24##     ClO.sub.4   (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.4                                         (2)                                                                                   ##STR25##     SbF.sub.6   (CH.sub.2 CHF.sub.2 CH.sub.2 CHF.sub.2).                                      sub.4                                       (3)                                                                                   ##STR26##     AsF.sub.6   (C.sub.3 F.sub.7 C.sub.3 F.sub.7).sub.4                                       2                                           (4)                                                                                   ##STR27##     ClO.sub.4   (CH.sub.2 C.sub.2 F.sub.5 CH.sub.2                                            C.sub.2 F.sub.5).sub.4                      (5)                                                                                   ##STR28##     BF.sub.4    (C.sub.2 F.sub.5 C.sub.2 F.sub.5).sub.4                                       .                                           (6)                                                                                   ##STR29##     SbF.sub.6                                                                                  ##STR30##                                  (7)                                                                                   ##STR31##     I           (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                    (8)                                                                                   ##STR32##     Br          (C.sub.4 F.sub.9 C.sub.4 F.sub.9).sub.4     (9)                                                                                   ##STR33##     ClO.sub.4   (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                    (10)                                                                                  ##STR34##                                                                                    ##STR35##  (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (11)                                                                                  ##STR36##     SbF.sub.6   (CH.sub.2 (CF.sub.2).sub.4 H CH.sub.2                                         (CF.sub.2).sub.4 H).sub.4                   (12)                                                                                  ##STR37##     ClO.sub.4   (CH.sub.2 (CF.sub.2).sub.2 CF.sub.3                                           CH.sub.2 (CF.sub.2).sub.2 CF.sub.3).sub.                                      4                                           (13)                                                                                  ##STR38##     Cl          (CF.sub.2 CF.sub.2 CH.sub.3 CF.sub.2                                          CF.sub.2 CH.sub.3).sub.4                    (14)                                                                                  ##STR39##     NO.sub.2                                                                                   ##STR40##                                  (15)                                                                                  ##STR41##     AsF.sub.6                                                                                  ##STR42##                                  [I]-(A)-(16)                                                                          ##STR43##     ClO.sub.4   (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.3 CHFCF.sub.3).sub.4                 (17)                                                                                  ##STR44##     Br                                                                                         ##STR45##                                  (18)                                                                                  ##STR46##     SbF.sub.6   (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.4                                         (19)                                                                                  ##STR47##     AsF.sub.6   (CH.sub.2 C.sub.2 F.sub.5 CH.sub.2                                            C.sub.2 F.sub.5).sub.4                      (20)                                                                                  ##STR48##     ClO.sub.4                                                                                  ##STR49##                                  (21)                                                                                  ##STR50##     I           ((CF.sub.2).sub.7 CF.sub.3                                                    (CF.sub.2).sub.7 CF.sub.3).sub.4            (22)                                                                                  ##STR51##     NO.sub.2    ((CF.sub.2).sub.3 CF.sub.3                                                    (CF.sub.2).sub.3 CF.sub.3).sub.4            (23)                                                                                  ##STR52##     CH.sub.3 SO.sub.3                                                                         (C.sub.2 F.sub.5 C.sub.2 F.sub.5).sub.4     (24)                                                                                  ##STR53##     AsF.sub.6   (C.sub.3 F.sub.7 C.sub.3 F.sub.7)                                             (C.sub.3 H.sub.7 C.sub.3 H.sub.7).sub.3     (25)                                                                                  ##STR54##     CI          (CH.sub.2 CH.sub.2 CF.sub.3 CH.sub.2                                          CH.sub.2 CF.sub.3).sub.2 (C.sub.2                                             H.sub.4 OCH.sub.3 C.sub.2 H.sub.4                                             OCH.sub.3 ).sub.2                           (26)                                                                                  ##STR55##     ClO.sub.4   (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.3 (C.sub.3 H.sub.7 C.sub.3                                             H.sub.7)                                    (27)                                                                                  ##STR56##     Br          (CH.sub.2 CHF.sub.2 CH.sub.2 CHF.sub.2).                                      sub.4                                       (28)                                                                                  ##STR57##     ClO.sub.4                                                                                  ##STR58##                                  (29)                                                                                  ##STR59##     SbF.sub.6   (CF.sub.3 CF.sub.3).sub.2 (C.sub.2                                            H.sub.5 C.sub.2 H.sub.5).sub.2              (30)                                                                                  ##STR60##     I           (CH.sub.2 (CF.sub.2).sub.4 H CH.sub.2                                         (CF.sub.2).sub.4 H).sub.3 (n-C.sub.4                                          H.sub.9 n-C.sub.4 H.sub.9)                  [I]-(A)-(31)                                                                          ##STR61##     ClO.sub.4   (C.sub.2 H.sub.4 OCF.sub.3 C.sub.2                                            H.sub.4 OCF.sub.3).sub.4                    (32)                                                                                  ##STR62##     I           (CFCF.sub.2 CFCF.sub.2).sub.4               (33)                                                                                  ##STR63##     AsF.sub.6   (CH.sub.2 CH.sub.2 CFCF.sub.2 CH.sub.2                                        CH.sub.2 CFCF.sub.2).sub.4                  (34)                                                                                  ##STR64##     Br                                                                                         ##STR65##                                  (35)                                                                                  ##STR66##     SbF.sub.6   (CF.sub.2 CF.sub.2 OCF.sub.2 CF.sub.3                                         CF.sub.2 CF.sub.2 OCF.sub.2 CF.sub.3).su                                      b.4                                         (36)                                                                                  ##STR67##     NO.sub.2    (CF.sub.2 CF.sub.2 CF.sub.2 CF.sub.2).su                                      b. 4                                        (37)                                                                                  ##STR68##     ClO.sub.4                                                                                  ##STR69##                                  (38)                                                                                  ##STR70##     Cl          (C.sub.2 H.sub.4 OC.sub.2 F.sub.5                                             C.sub.2 H.sub.4 OC.sub.2 F.sub.5).sub.4     (39)                                                                                  ##STR71##     ClO.sub.4                                                                                  ##STR72##                                  (40)                                                                                  ##STR73##     AsF.sub.6   (CH.sub.2 CF.sub.2 CF.sub.2 OCH.sub.3                                         CH.sub.2 CF.sub.2 CF.sub.2 OCH.sub.3).su                                      b.4                                         (41)                                                                                  ##STR74##                                                                                    ##STR75##  (CH.sub.2 CF.sub.2 CF.sub.2 H CH.sub.2                                        CH.sub.2 CF.sub.2 H).sub.4                  (42)                                                                                  ##STR76##     SbF.sub.6                                                                                  ##STR77##                                  (43)                                                                                  ##STR78##     I           (CF.sub.2 CF.sub. 2 CHCH.sub.2 CF.sub.2                                       CF.sub.2 CHCH.sub.2).sub.2 (n-C.sub.3                                         H.sub.7 n-C.sub.3 H.sub.7).sub.2            [I]-(B)-(1)                                                                           ##STR79##     Cl          (C.sub.3 F.sub.7 C.sub.3 F.sub.7).sub.4     (2)                                                                                   ##STR80##     SbF.sub.6   (CH.sub.2 CHF.sub.2 CH.sub.2 CHF.sub.2).                                      sub.4                                       (3)                                                                                   ##STR81##     AsF.sub.6   (CH.sub.2 CF.sub.3 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (4)                                                                                   ##STR82##     ClO.sub.4   (CH.sub.2 (CF.sub.2).sub.4 H CH.sub.2                                         (CF.sub.2).sub.4 H).sub.4                   (5)                                                                                   ##STR83##     Br          (C.sub.4 F.sub.9 C.sub.4 F.sub.9).sub.4     (6)                                                                                   ##STR84##     SbF.sub.6   (C.sub.2 F.sub.5 C.sub.2 F.sub.5).sub.4     (7)                                                                                   ##STR85##     CH.sub.3 SO.sub.3                                                                         (CF.sub.2 CF.sub.2 CH.sub.3 CF.sub.2                                          CF.sub.2 CH.sub.3).sub.4                    (8)                                                                                   ##STR86##     ClO.sub.4                                                                                  ##STR87##                                  (9)                                                                                   ##STR88##     I                                                                                          ##STR89##                                  (10)                                                                                  ##STR90##     BF.sub.4                                                                                   ##STR91##                                  (11)                                                                                  ##STR92##     SbF.sub.6   (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.2                                         (12)                                                                                  ##STR93##     ClO.sub.4   (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3)                       (13)                                                                                  ##STR94##     AsF.sub.6   (CH.sub.2 CF.sub.2 CF.sub.3 CH.sub.2                                          CF.sub.2 CF.sub.3).sub.2 (n-C.sub.4                                           H.sub.9 n-C.sub.4 H.sub.9).sub.2            (14)                                                                                  ##STR95##     CH.sub.3 CO                                                                                ##STR96##                                  (15)                                                                                  ##STR97##     ClO.sub.4   (CH.sub.2 CF.sub.2 CHCFCF.sub.3                                               CH.sub.2 C.sub.2 F.sub.5).sub.4             [I]-(C)-(1)                                                                           ##STR98##     SbF.sub.6   (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                    (2)                                                                                   ##STR99##     Br          (CF.sub.2 CF.sub. 3 CF.sub.2 CF.sub.3).s                                      ub.4                                        (3)                                                                                   ##STR100##    ClO.sub.4                                                                                  ##STR101##                                 (4)                                                                                   ##STR102##    AsF.sub.6   (CH.sub.2 (CF.sub.2).sub.2 CF.sub.3                                           CH.sub.2 (CF.sub.2).sub.2 CF.sub.3).sub.                                      4                                           (5)                                                                                   ##STR103##    SbF.sub.6   (CH.sub.2 CH.sub.2 CF.sub.2 CF.sub.3                                          CH.sub.2 CH.sub.2 CF.sub.2 CH.sub.3).sub                                      .4                                          (6)                                                                                   ##STR104##    I           (CH.sub.2 CH.sub.2 CF.sub.3 CH.sub.2                                          CH.sub.2 CF.sub.3).sub.4                    (7)                                                                                   ##STR105##    ClO.sub.4   (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (8)                                                                                   ##STR106##    AsF.sub.6   (CF.sub.3  CF.sub.3).sub.4                  (9)                                                                                   ##STR107##    CF.sub.3 SO.sub.3                                                                          ##STR108##                                 (10)                                                                                  ##STR109##    NO.sub.2    (CH.sub.2 C.sub.2 F.sub.5 CH.sub.2                                            C.sub.2 F.sub.5).sub.2 (C.sub.3 H.sub.7                                       C.sub.3 H.sub.7).sub.2                      (11)                                                                                  ##STR110##    ClO.sub.4   (CH.sub.2 CHF.sub.2 CH.sub.2 CHF.sub.2).                                      sub.3 (CH.sub.2 OCH.sub.3 CH.sub.2                                            OCH.sub.3)                                  (12)                                                                                  ##STR111##    SbF.sub.6   (CF.sub.2 CF.sub.2 OCF.sub.2 CF.sub.2).s                                      ub.4                                        (13)                                                                                  ##STR112##    AsF.sub.6   (CH.sub.2 CH.sub. 2 OCF.sub.3 CH.sub.2                                        CH.sub.2 OCF.sub.3).sub.4                   (14)                                                                                  ##STR113##    ClO.sub.4   (CH.sub.2 CH.sub.2 CFCF.sub.2 CH.sub.2                                        CH.sub.2 CFCF.sub.2).sub.4                  (15)                                                                                  ##STR114##    I           (n-C.sub.4 F.sub.9 n-C.sub.4 F.sub.9).su                                      b.4                                         [I]-(D)-(1)                                                                           ##STR115##    Cl          (n-C.sub.4 F.sub.9 n-C.sub.4 F.sub.9).su                                      b.4                                         (2)                                                                                   ##STR116##    AsF.sub.6   (CH.sub.2 CF.sub.2 CF.sub.3 CH.sub.2                                          CF.sub.2 CF.sub.3).sub.4                    (3)                                                                                   ##STR117##    Br          (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                    (4)                                                                                   ##STR118##    ClO.sub.4   (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (5)                                                                                   ##STR119##    SbF.sub.6   (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.4                                         (6)                                                                                   ##STR120##    I                                                                                          ##STR121##                                 (7)                                                                                   ##STR122##    ClO.sub.4                                                                                  ##STR123##                                 (8)                                                                                   ##STR124##    AsF.sub.6   (C.sub.3 F.sub.7 C.sub.3 F.sub.7).sub.4     (9)                                                                                   ##STR125##    SbF.sub.6   (CH.sub.2 (CF.sub.2).sub.4 H CH.sub.2                                         (CF.sub.2).sub.4 H).sub. 4                  (10)                                                                                  ##STR126##    ClO.sub.4                                                                                  ##STR127##                                 (11)                                                                                  ##STR128##    NO.sub.2    (CH.sub.2 (CF.sub.2).sub.2 CF.sub.3                                           CH.sub.2 (CF.sub.2).sub.2 CF.sub.3).sub.                                      4                                           (12)                                                                                  ##STR129##    CF.sub.3 SO.sub.3                                                                         (C.sub.3 H.sub.6 OCF.sub.3 C.sub.3                                            H.sub.6 OCF.sub.3).sub.2 (CH.sub.2                                            CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2).sub                                      .2                                          (13)                                                                                  ##STR130##    ClO.sub.4                                                                                  ##STR131##                                 (14)                                                                                  ##STR132##    I           (CF.sub.3 CF.sub.3) (C.sub.6 H.sub.13                                         C.sub.6 H.sub.13).sub.3                     (15)                                                                                  ##STR133##    SbF.sub.6                                                                                  ##STR134##                                 [I]-(E)-(1)                                                                           ##STR135##    Cl          (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                    (2)                                                                                   ##STR136##    NO.sub.2    (C.sub.3 F.sub.7 C.sub.3 F.sub.7).sub.4     (3)                                                                                   ##STR137##    AsF.sub.6   (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (4)                                                                                   ##STR138##    SbF.sub.6   (CH.sub.2 C.sub.2 F.sub.5 CH.sub.2                                            C.sub.2 F.sub.5).sub.4                      (5)                                                                                   ##STR139##    ClO.sub.4                                                                                  ##STR140##                                 (6)                                                                                   ##STR141##    Br          (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.4                                         (7)                                                                                   ##STR142##    ClO.sub.4   (n-C.sub.4 F.sub.9 n-C.sub.4 F.sub.9).su                                      b.4                                         (8)                                                                                   ##STR143##    SbF.sub.6   (C.sub.2 F.sub.5 C.sub.2 F.sub.5).sub.2                                       (C.sub.2 H.sub.5 C.sub.2 H.sub.5).sub.2     (9)                                                                                   ##STR144##                                                                                   ##STR145##                                                                                ##STR146##                                 (10)                                                                                  ##STR147##    I           (CF.sub.2 CF.sub.2 OCF.sub.2 CF.sub.2).s                                      ub.4                                        (11)                                                                                  ##STR148##    ClO.sub.4   (CF.sub.2 CHCH.sub.2 CF.sub.2 CHCH.sub.2                                      ).sub.4                                     (12)                                                                                  ##STR149##    AsF.sub.6                                                                                  ##STR150##                                 (13)                                                                                  ##STR151##    SbF.sub.6   (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                    (14)                                                                                  ##STR152##    Br          ((CF.sub.2).sub.7 CF.sub.3                                                    (CF.sub.2).sub.7 CF.sub.3).sub.4            (15)                                                                                  ##STR153##    ClO.sub.4   (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.4                                         [II]-(A)-(1)                                                                          ##STR154##    ClO.sub.4   (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                    (2)                                                                                   ##STR155##                                                                                   ##STR156## (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (3)                                                                                   ##STR157##    SbF.sub.6   (CH.sub.2 (CF.sub.2).sub.4 H CH.sub.2                                         (CF.sub.2).sub.4 H).sub.4                   (4)                                                                                   ##STR158##    ClO.sub.4   (CH.sub.2 (CF.sub.2).sub.2 CF.sub.3                                           CH.sub.2 (CF.sub.2).sub.2 CF.sub.                                             3).sub.4                                    (5)                                                                                   ##STR159##    Cl          (CF.sub.2 CF.sub.2 CH.sub.3 CF.sub.2                                          CF.sub.2 CH.sub.3).sub.4                    (6)                                                                                   ##STR160##    NO.sub.2                                                                                   ##STR161##                                 (7)                                                                                   ##STR162##    AsF.sub.6                                                                                  ##STR163##                                 (8)                                                                                   ##STR164##    SbF.sub.6   (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.4                                         (9)                                                                                   ##STR165##    AsF.sub.6   (CH.sub.2 C.sub.2 F.sub.5 CH.sub.2                                            C.sub.2 F.sub.5).sub.4                      (10)                                                                                  ##STR166##    ClO.sub. 4                                                                                 ##STR167##                                 (11)                                                                                  ##STR168##    I           ((CF.sub.2).sub.7 CF.sub.3                                                    (CF.sub.2).sub.7 CF.sub.3).sub.4            (12)                                                                                  ##STR169##    NO.sub.2    ((CF.sub.2).sub.3 CF.sub.3                                                    (CF.sub.2).sub.3 CF.sub.3).sub.4            (13)                                                                                  ##STR170##    CH.sub.3 SO.sub.3                                                                         (C.sub.2 F.sub.5 C.sub.2 F.sub.5).sub.4     (14)                                                                                  ##STR171##    AsF.sub.6   (C.sub.3 F.sub.7 C.sub.3 H.sub.7)                                             (C.sub.3 H.sub.7 C.sub.3 H.sub.7).sub.3     (15)                                                                                  ##STR172##    Cl          (CH.sub.2 CH.sub.2 CF.sub.3 CH.sub.2                                          CH.sub.2 CF.sub.3).sub.2 (C.sub.2                                             H.sub.4 OCH.sub.3 C.sub.2 H.sub.4                                             OCH.sub.3).sub.2                            [II]-(A)-(16)                                                                         ##STR173##    ClO.sub.4   (C.sub.2 H.sub.4 OCF.sub.3 C.sub.2                                            H.sub.4 OCF.sub.3).sub.4                    (17)                                                                                  ##STR174##    I           (CFCF.sub.2 CFCF.sub.2).sub.4               (18)                                                                                  ##STR175##    AsF.sub.6   (CH.sub.2 CH.sub.2 CFCF.sub.2 CH.sub.2                                        CH.sub.2 CFCF.sub.2).sub.4                  (19)                                                                                  ##STR176##    Br                                                                                         ##STR177##                                 (20)                                                                                  ##STR178##    SbF.sub.6   (CF.sub.2 CF.sub.2 OCF.sub.2 CF.sub.3                                         CF.sub.2 CF.sub.2 OCF.sub.2 CF.sub.3).su                                      b.4                                         (21)                                                                                  ##STR179##    NO.sub.2    (CF.sub.2 CF.sub.2 CF.sub.2 CF.sub.2).su                                      b.4                                         (22)                                                                                  ##STR180##    ClO.sub.4                                                                                  ##STR181##                                 (23)                                                                                  ##STR182##    Cl          (C.sub.2 H.sub.4 OC.sub.2 F.sub.5                                             C.sub.2 H.sub.4 OC.sub.2 F.sub.5).sub.4     (24)                                                                                  ##STR183##    ClO.sub.4                                                                                  ##STR184##                                 (25)                                                                                  ##STR185##    AsF.sub.6   (CH.sub.2 CF.sub.2 CF.sub.2 OCH.sub.3                                         CH.sub.2 CF.sub.2 CF.sub.2 OCH.sub.3).su                                      b.4                                         (26)                                                                                  ##STR186##                                                                                   ##STR187## (CH.sub.2 CF.sub.2 CF.sub.2 H CH.sub.2                                        CH.sub.2 CF.sub.2 H).sub.4                  (27)                                                                                  ##STR188##    SbF.sub.6                                                                                  ##STR189##                                 (28)                                                                                  ##STR190##    ClO.sub.4   (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.4                                         (29)                                                                                  ##STR191##    SbF.sub.6   (CH.sub.2 CHF.sub.2 CH.sub.2 CHF.sub.2).                                      sub.4                                       (30)                                                                                  ##STR192##    AsF.sub.6   (C.sub.3 F.sub.7 C.sub.3 F.sub.7).sub.4     [II]-(B)-(1)                                                                          ##STR193##    ClO.sub.4                                                                                  ##STR194##                                 (2)                                                                                   ##STR195##    I           (CF.sub.3 CF.sub.3) (C.sub.6 H.sub.13                                         C.sub.6 H.sub.13).sub.3                     (3)                                                                                   ##STR196##    SbF.sub.6                                                                                  ##STR197##                                 (4)                                                                                   ##STR198##    AsF.sub.6   (CH.sub.2 CF.sub.2 CF.sub.3 CH.sub.2                                          CF.sub.2 CF.sub.3).sub.4                    (5)                                                                                   ##STR199##    Br          (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                    (6)                                                                                   ##STR200##    ClO.sub.4   (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (7)                                                                                   ##STR201##    SbF.sub.6   (CH.sub.2 CF.sub.3 CH.sub.2 CF.sub.3).su                                      b.4                                         (8)                                                                                   ##STR202##    I                                                                                          ##STR203##                                 (9)                                                                                   ##STR204##    ClO.sub.4                                                                                  ##STR205##                                 (10)                                                                                  ##STR206##    AsF.sub.6   (C.sub.3 F.sub.7 C.sub.3 F.sub.7).sub.4     (11)                                                                                  ##STR207##    SbF.sub.6   (CH.sub.2 (CF.sub.2).sub.4 H CH.sub.2                                         (CF.sub.2).sub.4 H).sub.4                   (12)                                                                                  ##STR208##    ClO.sub.4                                                                                  ##STR209##                                 (13)                                                                                  ##STR210##    NO.sub.2    (CH.sub.2 (CF.sub.2).sub.2 CF.sub.3                                           CH.sub.2 (CF.sub.2).sub.2 CF.sub.3).sub.                                      4                                           [II]-(C)-(1)                                                                          ##STR211##    SbF.sub.6   (CH.sub.2 CF.sub.2 CH.sub.2 CF.sub.3).su                                      b.4                                         (2)                                                                                   ##STR212##    ClO.sub.4   (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (3)                                                                                   ##STR213##    AsF.sub.6   (CH.sub.2 CF.sub.2 CF.sub.3 CH.sub.2                                          CF.sub.2 CF.sub.3).sub.2 (n-C.sub.4                                           H.sub.9 n-C.sub.4 H.sub.9).sub.2            (4)                                                                                   ##STR214##    Cl          (C.sub.3 F.sub.7 C.sub.3 F.sub.7).sub.4     (5)                                                                                   ##STR215##    SbF.sub.6   (CH.sub.2 CHF.sub.2 CH.sub.2 CHF.sub.2).                                      sub.4                                       (6)                                                                                   ##STR216##    AsF.sub.6   (CH.sub.2 CF.sub.3 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 (7)                                                                                   ##STR217##    ClO.sub.4   (CH.sub.2 (CF.sub.2).sub.4 H CH.sub.2                                         (CF.sub.2).sub.4 H).sub.4                   (8)                                                                                   ##STR218##    Br          (C.sub.4 F.sub.9 C.sub.4 F.sub.9).sub.4     (9)                                                                                   ##STR219##    SbF.sub.6   (C.sub.2 F.sub.5 C.sub.2 F.sub.5).sub.4     (10)                                                                                  ##STR220##    CH.sub.3 SO.sub.3                                                                         (CF.sub.2 CF.sub.2 CH.sub.3 CF.sub.2                                          CF.sub. 2 CH.sub.3).sub.4                   (11)                                                                                  ##STR221##    ClO.sub.4                                                                                  ##STR222##                                 (12)                                                                                  ##STR223##    I                                                                                          ##STR224##                                 (13)                                                                                  ##STR225##    BF.sub.4                                                                                   ##STR226##                                 [II]-(D)-(1)                                                                          ##STR227##    SbF.sub.6   (CH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2                                        F).sub.4                                     (2)                                                                                  ##STR228##    Br          (CF.sub.2 CF.sub.3 CF.sub.2 CF.sub.3).su                                      b.4                                         (3)                                                                                   ##STR229##    AsF.sub.6   (CF.sub.3 CF.sub.3).sub.4                   (4)                                                                                   ##STR230##    CF.sub.3 SO.sub.3                                                                          ##STR231##                                 (5)                                                                                   ##STR232##    NO.sub.2    (CH.sub.2 C.sub.2 F.sub.5 CH.sub.2                                            C.sub.2 F.sub.5).sub.2 (C.sub.3 H.sub.7                                       C.sub.3 H.sub.7).sub.2                      (6)                                                                                   ##STR233##    ClO.sub.4   (CH.sub.2 CHF.sub.2 CH.sub.2 CHF.sub.2).                                      sub.3 (CH.sub.2 OCH.sub.3 CH.sub.2                                            OCH.sub.3)                                  (7)                                                                                   ##STR234##    SbF.sub.6   (CF.sub.2 CF.sub.2 OCF.sub.2 CF.sub.2).s                                      ub.4                                        (8)                                                                                   ##STR235##    AsF.sub.6   (CH.sub.2 CH.sub.2 OCF.sub.3 CH.sub.2                                         CH.sub.2 OCF.sub.3).sub.4                   (9)                                                                                   ##STR236##    ClO.sub.4   (CH.sub.2 CH.sub.2 CFCF.sub.2 CH.sub.2                                        CH.sub.2 CFCF.sub.2).sub.4                  (10)                                                                                  ##STR237##    I           (n-C.sub.4 F.sub.9 n-C.sub.4 F.sub.9).su                                      b.4                                         (11)                                                                                  ##STR238##    AsF.sub.6   (CH.sub.2 (CF.sub.2).sub.2 CF.sub.3                                           CH.sub.2 (CF.sub.2).sub.2 CF.sub.3).sub.                                      4                                           (12)                                                                                  ##STR239##    SbF.sub.6   (CH.sub.2 CH.sub.2 CF.sub.2 CF.sub.3                                          CH.sub.2 CH.sub.2 CF.sub.2 CF.sub.3).sub                                      .4                                          (13)                                                                                  ##STR240##    I           (CH.sub.2 CH.sub.2 CF.sub.3 CH.sub.2                                          CH.sub.2 CF.sub.3).sub.4                    (14)                                                                                  ##STR241##    ClO.sub.4   (CH.sub.2 CF.sub.2 CHFCF.sub.3 CH.sub.2                                       CF.sub.2 CHFCF.sub.3).sub.4                 __________________________________________________________________________

The infrared-absorptive compounds of the present invention, representedby formulas (I) and (II) can be synthesized by the methods disclosed inU.S. Pat. Nos. 3,251,881, 3,575,871 and 3,484,467 and Japanese PatentApplication Laid-Open No. 61-69991. For example, they can be synthesizedaccording to the following scheme. ##STR242## The amino compoundobtained by the above Ullmann reaction and reduction reaction issubjected to selective substitution to substitute the hydrogen atom(s)with the RF or other organic residual Group(s) by alkylation,alkenylation or aralkylation, followed by oxidation reaction to give theend product.

Stated more specifically, for example, in the course of the abovealkylation, the amino compound obtained by the above reaction is reactedwith an 8-fold amount of 2,2,2-trifluoroethyl iodide, whereby analkylated intermediate product is obtained. This product is furtheroxidized by silver salt oxidation or electrolytic oxidation to obtainthe end product.

In an instance in which R₀ to R₇ are asymmetrically formed, theselective substitution must be multi-stepwise carried out. In view ofcost, R₀ to R₇ may preferably be the same.

In the course of the alkylation, for example, an. alkylating agentcapable of forming in combination of R₀ and R₁ a heterocyclic ringtogether with a nitrogen atom and also having a fluorine atom, statedmore specifically, 1,4-dibromobutane or the like having a fluorine atomis used, whereby a heterocyclic ring having a fluorine atom can beformed in the combination of R₀ and R₁.

The above infrared-absorptive compounds of the present invention have amaximum absorption wavelength of 900 nm or more and an absorptivitycoefficient of from several tens of thousands to hundred and severaltens of thousands, showing a great absorption peak.

Such compounds can be used in thermal insulating films, sunglasses, etc.

Next, the infrared-absorptive compound according to a second embodimentof the present invention is a compound represented by the followingformula (III) or (IV). ##STR243## In formulas (III) and (IV), R'₁ toR'₁₆ each represent a hydrogen atom or a monovalent organic residualgroup.

The monovalent organic residual group may include those exemplified by asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedalkenyl group, a substituted or unsubstituted aryl group, a substitutedor unsubstituted aralkyl group and also an alkynyl group. For example,the unsubstituted alkyl group may include those exemplified by a methylgroup, an ethyl group, a n-propyl group, an iso-propyl group, a n-butylgroup, an iso-butyl group, a t-butyl group, a n-amyl group, a t-amylgroup, a n-hexyl group, a n-octyl group and a t-octyl group. Thesubstituted alkyl group may include, for example, halogenated alkylgroups such as a 2-chloroethyl group and a 2-chloropropyl group,hydroxyalkyl groups such as a 2-hydroxyethyl group, a 3-hydroxypropylgroup and a 4-hydroxybutyl group, acetoxy alkyl groups such as a2-acetoxyethyl group and 2-acetoxypropyl group, carboxyalkyl groups suchas a carboxymethyl group, a 2-carboxyethyl group end a 3-carboxypropylgroup, and alkoxyalkyl groups such as a methoxymethyl group, amethoxyethyl group, a methoxypropyl group, a methoxybutyl group, anethoxymethyl group, an ethoxyethyl group, an ethoxypropy1 group, anethoxybutyl group and a propoxymethyl group. The alkenyl group mayinclude those exemplified by a vinyl group, a propenyl group, a butenylgroup, a pentenyl group, a hexenyl group, a heptenyl group and anoctenyl group, and also any of these alkenyl groups whose hydrogen atomhas been substituted with a halogen atom, a hydroxyl group, an acetoxylgroup, a carboxyl group or an alkoxyl group. The aralkyl group mayinclude those exemplified by a benzyl group, a 2-methylbenzyl group, ap-phenylmethyl group, a 2-phenylpropyl group, a 3-phenylpropyl group, anα-naphthylmethyl group and a β-naphthylethyl group, and also any ofthese aralkyl groups whose hydrogen atom has been substituted with ahalogen atom as exemplified by a p-chlorobenzyl group, and any of thesearalkyl groups whose hydrogen atom has been substituted with a hydroxylgroup, an acetoxyl group, a carboxyl group or an alkoxyl group. Thesubstituted or unsubstituted aryl group may include those exemplified bya phenyl group, a naphthyl group, a tolyl group, a xylyl group, amethoxyphenyl group, a dimethoxyphenyl group, a trimethoxyphenyl group,an ethoxyphenyl group, a dimethylaminophenyl group, a diethylaminophenylgroup, a dipropylaminophenyl group, a dibenzylaminophenyl group, adiphenylaminophenyl group, a dimethoxymethylaminophenyl group and aditolylaminophenyl group. The alkynyl group may include thoseexemplified by a propagyl group, a butynyl group, a pentynyl group and ahexynyl group.

R'₁ to R'₁₆ may be the same or may be different one another.

R'₁ to R'₈ may be in at least one combination of combinations R'₁ andR'₂, R'₃ and R'₄, R'₅ and R'₆ and R'₇ and R'₈, a group of atomsnecessary to form a substituted or unsubstituted 5-membered ring, asubstituted or unsubstituted 6-membered ring or a substituted orunsubstituted 7-membered ring together with a nitrogen atom. The5-membered ring may include, for example, a pyrrolidine ring, the6-membered ring may include a piperidine ring, a morpholine ring and atetrahydropyridine group, and the 7-membered ring may include thecylcohexylamine ring represented by formula (VII) previously described.Of the substituents R'₁ to R'₈, two or more of the above combinationsmay be made to have the heterocyclic structure described above, and insuch an instance, the structure may be the same or different from eachother.

As for R'₉ to R'₁₆, they may be in at least one combination ofcombinations R'₉ and R'₁₀, R'₁₀ and R'₁₁, R'₁₁ and R'₁₂, R'₁₃ and R'₁₄,R'₁₄ and R'₁₅ and R'₁₅ and R'₁₆, a group of atoms necessary to form acondensed ring. Here, the condensed ring may include aromatic rings asexemplified by a benzene ring, a naphthalene ring, a chlorobenzene ring,a bromobenzene ring, a methylbenzene ring, an ethylbenzene ring, amethoxybenzene ring and an ethoxybenzene ring, heterocyclic rings asexemplified by a furan ring, a benzofuran ring, a pyrrole ring, athiophene ring, a pyridine ring, a quinoline ring and a thiazole ring,and aliphatic rings as exemplified by a dimethylene ring, a trimethylenering and a tetramethylene ring.

The infrared-absorptive compounds represented by formulas (III) and (IV)described above can bring about a much more improvement in heatresistance than the conventional aminium salt compounds or diimoniumsalt compounds. The reason why the infrared-absorptive compoundsrepresented by formulas (III) and (IV) show superior heat resistance isunclear. It is presumed that the central skeleton of the compound,formed of a rigid polycyclic aromatic ring such as the anthracene ringcontributes the greater improvement in heat resistance.

Incidentally, in the infrared-absorptive compounds represented byformulas (III) and (IV), at least one of R'₁ to R'₈ may be analkoxyalkyl group or any of the R'₉ to R'₁₆ substituted on the centralskeleton anthracene ring may be a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 5 carbon atoms as exemplified by amethyl group, an ethyl group, a propyl group, a t-butyl group, amethoxyethyl group or an ethoxyethyl group, a substituted orunsubstituted alkoxyl group having 1 to 5 carbon atoms as exemplified bya methoxy group, an ethoxy group, a propoxy group or a butoxy group, ahalogen atom as exemplified by fluorine, chlorine, bromine or iodine, ahydroxy group, or a cyano group. In such an instance, the heatresistance of the infrared-absorptive compounds can be improved and alsothe solvent solubility thereof can be improved.

The heat resistance and solvent solubility of the infrared-absorptivecompounds can also be improved when among R'₉ to R'₁₆, any ofcombinations R'₉ and R'₁₀, R'₁₀ and R'₁₁, R'₁₁ and R'₁₂, R'₁₂ and R'₁₃,R'₁₃ and R'₁₄, R'₁₄ and R'₁₅ and R'₁₅ and R'₁₆ forms a condensed ringand a combination or combinations R'₁₀ and R'₁₁ and/or R'₁₄ and R'₁₅form(s) a benzene ring.

X.sup.⊖ represents the same anionic residual group as previouslydescribed.

Examples of the infrared-absorptive compounds of formulas (III) and (IV)according to the present invention are shown below. In the presentinvention, examples are by no means limited to these.

The following exemplary compounds (III)-(1) to (IV)-(35) are set out inthe manner simplified as follows:

For example, in the infrared-absorptive compounds of formulas (III) and(IV), compounds having the following structures (D) and (E) arerespectively indicated as shown below.

    __________________________________________________________________________    (D)                                                                               ##STR244##                                                                (E)                                                                               ##STR245##                                                                 ##STR246##                                                                             ##STR247##                                                                                ##STR248##                                                                        ##STR249##                                                                             ##STR250##                                                                              ##STR251##                                                                             ##STR252##              __________________________________________________________________________    (D)                                                                                     ##STR253## ClO.sub.4                                                                         CH.sub.2 OCH.sub.3  CH.sub.2 OCH.sub.3                                                 CH.sub.2 OCH.sub.3  CH.sub.2 OCH.sub.3                                                   CH.sub.2 OCH.sub.3  CH.sub.2                                                 OCH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                            CH.sub.2 OCH.sub.3       (E)                                                                                     ##STR254## SbF.sub.6                                                                         CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2 CH.sub.2 CH.sub.2                                                    CH.sub.2 CH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2        __________________________________________________________________________

      ##STR255##      ##STR256##      ##STR257##      ##STR258##      ##STR259##      ##STR260##      ##STR261##              [III]-(1)      ##STR262##      ClO.sub.4 CH.sub.2 OCH.sub.3 ,CH.sub.2 OCH.sub.3 CH.sub.2      OCH.sub.3,CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3     CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3      [III]-(2)     ##STR263##      BF.sub.4 C.sub.2 H.sub.5,C.sub.2 H.sub.5 C.sub.2 H.sub.5,C.sub.2     H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5     [III]-(3)      ##STR264##      SbF.sub.6 C.sub.2 H.sub.5,C.sub.2 H.sub.5 C.sub.2 H.sub.5,C.sub.2     H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5     [III]-(4)      ##STR265##      Br      ##STR266##      ##STR267##      ##STR268##      ##STR269##      [III]-(5)     ##STR270##      ClO.sub.4 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3      H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3     H.sub.7,n-C.sub.3 H.sub.7      [III]-(6)     ##STR271##      SbF.sub.6 iso-C.sub.3 H.sub.7,iso-C.sub.3 H.sub.7 iso-C.sub.3      H.sub.7,iso-C.sub.3 H.sub.7 iso-C.sub.3 H.sub.7,iso-C.sub.3 H.sub.7     iso-C.sub.3 H.sub.7,iso-C.sub.3 H.sub.7      [III]-(7)     ##STR272##      CH.sub.3 SO.sub.4 C.sub.3 H.sub.6 OC.sub.3 H.sub.7,C.sub.3 H.sub.6     OC.sub.3 H.sub.7 C.sub.3 H.sub.6 OC.sub.3 H.sub.7,C.sub.3 H.sub.6     OC.sub.3 H.sub.7 C.sub.3 H.sub.6 OC.sub.3 H.sub.7,C.sub.3 H.sub.6     OC.sub.3 H.sub.7 C.sub.3 H.sub.6 OC.sub.3 H.sub.7,C.sub.3 H.sub.6     OC.sub.3 H.sub.7      [III]-(8)     ##STR273##      ClO.sub.4 CH.sub.2 CHCH.sub.2,CH.sub.2 CHCH.sub.2 CH.sub.2      CHCH.sub.2,CH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2,CH.sub.2 CHCH.sub.2     CH.sub.2 CHCH.sub.2,CH.sub.2 CHCH.sub.2      [III]-(9)     ##STR274##      AsF.sub.6 C.sub.2 H.sub.4 CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2 C.sub.2     H.sub.4 CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2 C.sub.2 H.sub.4            C      CHCH.sub.2,.sub.2 H.sub.4 CHCH.sub.2 C.sub.2 H.sub.4 CHCH.sub.2,C.sub.2     H.sub.4 CHCH.sub.2      [III]-(10)     ##STR275##      ClO.sub.4 n-C.sub.4 H.sub.9,n-C.sub.4 H.sub.9 n-C.sub.4      H.sub.9,n-C.sub.4 H.sub.9 n-C.sub.4 H.sub.9,n-C.sub.4 H.sub.9 n-C.sub.4     H.sub.9,n-C.sub.4 H.sub.9      [III]-(11)     ##STR276##      Cl n-C.sub.10 H.sub.21,n-C.sub.10 H.sub.21 n-C.sub.10      H.sub.21,n-C.sub.10 H.sub.21 n-C.sub.10 H.sub.21,n-C.sub.10 H.sub.21     n-C.sub.10 H.sub.21,n-C.sub.10 H.sub. 21      [III]-(12)     ##STR277##      ClO.sub.4 C.sub.2 H.sub.4 CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2 C.sub.2     H.sub.4 CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2 C.sub.2 H.sub.4            C      CHCH.sub.2,.sub.2 H.sub.4 CHCH.sub.2 C.sub.2 H.sub.4 CHCH.sub.2,C.sub.2     H.sub.4 CHCH.sub.2      [III]-(13)     ##STR278##      ClO.sub.4 C.sub.2 H.sub.4 OC.sub.2 H.sub.5,C.sub.2 H.sub.4 OC.sub.2     H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.5,C.sub.2 H.sub.4 OC.sub.2     H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.5,C.sub.2 H.sub.4 OC.sub.2     H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.5,C.sub.2 H.sub.4 OC.sub.2     H.sub.5      [III]-(14)     ##STR279##      SbF.sub.6 C.sub.2 H.sub.4 OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2     H.sub.4 OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.4      OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.4 OCH.sub.3,C.sub.2     H.sub.4 OCH.sub.3      [III]-(15)     ##STR280##      ##STR281##      n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.4 H.sub.9,n-C.sub.4 H.sub.9 n     -C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.4 H.sub.9,n-C.sub.4 H.sub.9     [III]-(16)      ##STR282##      SbF.sub.6 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 CH.sub.2      [ III]-(17)     ##STR283##      ClO.sub.4      ##STR284##      ##STR285##      ##STR286##      ##STR287##      [III]-(18)     ##STR288##      ClO.sub.4 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 OCH.sub.2 CH.sub.2      [III]-(19)     ##STR289##      NO.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2      [III]-(20)     ##STR290##      SbF.sub.6 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2                       C      CH.sub.2 CHC(CH.sub.3)H.sub.2 C(CH.sub.3).sub.2      CH.sub.2 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2      CH.sub.2 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2  [III]-(21)      ##STR291##      ClO.sub.4 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3      H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.5 H.sub.11,n-C.sub.5 H.sub.11     n-C.sub.5 H.sub.11,n-C.sub.5 H.sub.11      [III]-(22)     ##STR292##      I C.sub.3 H.sub.7 OH,C.sub.3 H.sub.7 OH C.sub.3 H.sub.7 OH,C.sub.3     H.sub.7 OH C.sub.3 H.sub.7 OH,C.sub.3 H.sub.7 OH C.sub.3 H.sub.7     OH,C.sub.3 H.sub.7 OH      [III] -(23)     ##STR293##      ClO.sub.4 C.sub.2 H.sub.5,C.sub.3 H.sub.7 C.sub.2 H.sub.5,C.sub.3     H.sub.7 C.sub.2 H.sub.5,C.sub.3 H.sub.7 C.sub.2 H.sub.5,C.sub.3 H.sub.7     [III]-(24)      ##STR294##      Br      ##STR295##      n-C.sub.5 H.sub.11,n-C.sub.5 H.sub.11 n-C.sub.5 H.sub.11,n-C.sub.5     H.sub.11 n-C.sub.5 H.sub.11,n-C.sub.5 H.sub.11      [III]-(25)     ##STR296##      SbF.sub.6      ##STR297##      ##STR298##      ##STR299##      ##STR300##      [III]-(26)     ##STR301##      ClO.sub.4 C.sub.2 H.sub.4 CCH,C.sub.2 H.sub.4 CCH C.sub.2 H.sub.4     CCH,C.sub.2 H.sub.4 C CH C.sub.2 H.sub.4 CCH,C.sub.2 H.sub.4 CCH C.sub.2     H.sub.4 CCH,C.sub.2 H.sub.4 CCH      [III]-(27)     ##STR302##      I C.sub.3 H.sub.6 C CH,C.sub.3 H.sub.6 CCH C.sub.3 H.sub.6 CCH,C.sub.3     H.sub.6 C CH C.sub.3 H.sub.6 CCH,C.sub.3 H.sub.6 CCH C.sub.3 H.sub.6     C     CCH,.sub.3 H.sub.6 CCH      [III]-(28)     ##STR303##      SbF.sub.6 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3      H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3     H.sub.7,n-C.sub.3 H.sub.7      [III]-(29)     ##STR304##      ClO.sub.4 C.sub.6 H.sub.4 Cl,C.sub.6 H.sub.4 Cl C.sub.6 H.sub.4     Cl,C.sub.6 H.sub.4 CL C.sub.6 H.sub.4 Cl,C.sub.6 H.sub.4 Cl C.sub.6     H.sub.4 Cl,C.sub.6 H.sub.4 Cl      [III]-(30)     ##STR305##      AsF.sub.6 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3      H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3     H.sub.7,n-C.sub.3 H.sub.7      [III]-(31)     ##STR306##      ClO.sub.4      ##STR307##      ##STR308##      ##STR309##      ##STR310##      [III]-(32)     ##STR311##      BF.sub.4 CH.sub.3,CH.sub.3 CH.sub.3,CH.sub.3 CH.sub.3,CH.sub.3 CH.sub.3,C     H.sub.3      [III]-(33)     ##STR312##      Br C.sub.2 H.sub.4 Cl,C.sub.2 H.sub.4 Cl C.sub.2 H.sub.4 Cl,C.sub.2     H.sub.4 Cl C.sub.2 H.sub.4 Cl,C.sub.2 H.sub.4 Cl C.sub.2 H.sub.4     Cl,C.sub.2 H.sub.4 Cl      [III]-(34)     ##STR313##      ClO.sub.4 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2                       C      CH.sub.2 CHC(CH.sub.3)H.sub.2 C(CH.sub.3).sub.2      CH.sub.2 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2      CH.sub.2 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2  [III]-(35)      ##STR314##      SbF.sub.6 C.sub.2 H.sub.4 OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2     H.sub.4 OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.5,C.sub.2     H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5      [III]-(36)     ##STR315##      ClO.sub.4 CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3 CH.sub.2      OCH.sub.3,CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3     CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3      [IV]-(1)     ##STR316##      ClO.sub.4 CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3 CH.sub.2      OCH.sub.3,CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3     CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3      [IV]-(2)     ##STR317##      BF.sub.4 C.sub.2 H.sub.5,C.sub.2 H.sub.5 C.sub.2 H.sub.5,C.sub.2     H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5     [IV]-(3)      ##STR318##      SbF.sub.6 C.sub.2 H.sub.5,C.sub.2 H.sub.5 C.sub.2 H.sub.5,C.sub.2     H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5     [IV]-(4)      ##STR319##      Cl      ##STR320##      ##STR321##      ##STR322##      ##STR323##      [IV]-(5)     ##STR324##      ClO.sub.4 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3      H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3     H.sub.7,n-C.sub.3 H.sub.7      [IV]-(6)     ##STR325##      SbF.sub.6 iso-C.sub.3 H.sub.7,iso-C.sub.3 H.sub.7 iso-C.sub.3      H.sub.7,iso-C.sub.3 H.sub.7 iso-C.sub.3 H.sub.7,iso-C.sub.3 H.sub.7     iso-C.sub.3 H.sub.7,iso-C.sub.3 H.sub.7      [IV]-(7)     ##STR326##      CH.sub.3 SO.sub.4 C.sub.3 H.sub.6 OC.sub.3 H.sub.7,C.sub.3 H.sub.6     OC.sub.3 H.sub.7 C.sub.3 H.sub. 6 OC.sub.3 H.sub.7,C.sub.3 H.sub.6     OC.sub.3 H.sub.7 C.sub.3 H.sub.6 OC.sub.3 H.sub.7,C.sub.3 H.sub.6     OC.sub.3 H.sub.7 C.sub.3 H.sub.6 OC.sub.3 H.sub.7,C.sub.3 H.sub.6     OC.sub.3 H.sub.7      [IV]-(8)     ##STR327##      ClO.sub.4 CH.sub.2 CHCH.sub.2,CH.sub.2 CHCH.sub.2 CH.sub.2      CHCH.sub.2,CH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2,CH.sub.2 CHCH.sub.2     CH.sub.2 CHCH.sub.2,CH.sub.2 CHCH.sub.2      [IV]-(9)     ##STR328##      AsF.sub.6 C.sub.2 H.sub.4 CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2 C.sub.2     H.sub.4 CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2 C.sub.2 H.sub.4            C      CHCH.sub.2,.sub.2 H.sub.4 CHCH.sub.2 C.sub.2 H.sub.4      CH CH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2      [IV]-(10)     ##STR329##      ClO.sub.4 n-C.sub.4 H.sub.9,n-C.sub.4 H.sub.9 n-C.sub.4      H.sub.9,n-C.sub.4 H.sub.9 n-C.sub.4 H.sub.9,n-C.sub.4 H.sub.9 n-C.sub.4     H.sub.9,n-C.sub.4 H.sub.9      [IV]-(11)     ##STR330##      Cl n-C.sub.10 H.sub.21,n-C.sub.10 H.sub.21 n-C.sub.10      H.sub.21,n-C.sub.10 H.sub.21 n-C.sub.10 H.sub.21,n-C.sub.10 H.sub.21     n-C.sub.10 H.sub.21,n-C.sub.10 H.sub.21      [IV]-(12)     ##STR331##      ClO.sub.4 C.sub.2 H.sub.4 CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2 C.sub.2     H.sub.4 CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2 C.sub.2 H.sub.4            C      CHCH.sub.2,.sub. 2 H.sub.4 CHCH.sub.2 C.sub.2 H.sub.4      CHCH.sub.2,C.sub.2 H.sub.4 CHCH.sub.2      [IV]-(13)     ##STR332##      ClO.sub.4 C.sub.2 H.sub.4 OC.sub.2 H.sub.5,C.sub.2 H.sub.4 OC.sub.2     H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.5,C.sub.2 H.sub.4 OC.sub.2     H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.5,C.sub.2 H.sub.4 OC.sub.2     H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.5,C.sub.2 H.sub.4 OC.sub.2     H.sub.5      [IV]-(14)     ##STR333##      SbF.sub.6 C.sub.2 H.sub.4 OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2     H.sub.4 OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.4      OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.4 OCH.sub.3,C.sub.2     H.sub.4 OCH.sub.3      [IV] -(15)     ##STR334##      ##STR335##      n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.4 H.sub.9,n-C.sub.4 H.sub.9 n     -C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.4 H.sub.9,n-C.sub.4 H.sub.9     [IV]-(16)      ##STR336##      SbF.sub.6 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 CH.sub.2      [IV]-(17)     ##STR337##      ClO.sub.4      ##STR338##      ##STR339##      ##STR340##      ##STR341##      [IV]-(18)     ##STR342##      ClO.sub.4 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 OCH.sub.2 CH.sub.2      [IV]-(19)     ##STR343##      NO.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2      [IV]-(20)     ##STR344##      SbF.sub.6 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2                       C      CH.sub.2 CHC(CH.sub.3)H.sub.2 C(CH.sub.3).sub.2      CH.sub.2 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2      CH.sub.2 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2  [IV]-(21)      ##STR345##      ClO.sub.4 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3      H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.5 H.sub.11,n-C.sub.5 H.sub.11     n-C.sub.5 H.sub.11,n-C.sub.5 H.sub.11      [IV]-(22)     ##STR346##      I C.sub.3 H.sub.7 OH,C.sub.3 H.sub.7 OH C.sub.3 H.sub.7 OH,C.sub.3     H.sub.7 OH C.sub.3 H.sub.7 OH,C.sub.3 H.sub.7 OH C.sub.3 H.sub.7     OH,C.sub.3 H.sub.7 OH      [IV]-(23)     ##STR347##      ClO.sub.4 C.sub.2 H.sub.5,C.sub.3 H.sub.7 C.sub.2 H.sub.5,C.sub.3     H.sub.7 C.sub.2 H.sub.5,C.sub.3 H.sub.7 C.sub.2 H.sub.5,C.sub.3 H.sub.7     [IV]-(24)      ##STR348##      Br      ##STR349##      n-C.sub.5 H.sub.11,n-C.sub.5 H.sub.11 n-C.sub.5 H.sub.11,n-C.sub.5     H.sub.11 n-C.sub.5 H.sub.11,n-C.sub.5 H.sub.11      [IV]-(25)     ##STR350##      SbF.sub.6      ##STR351##      ##STR352##      ##STR353##      ##STR354##      [IV]-(26)     ##STR355##      ClO.sub.4 C.sub.2 H.sub.4 CCH,C.sub.2 H.sub.4 CCH C.sub.2 H.sub.4     CCH,C.sub.2 H.sub.4 C  CH C.sub.2 H.sub.4 CCH,C.sub.2 H.sub.4 CCH     C.sub.2 H.sub.4 CCH,C.sub.2 H.sub.4 CCH      [IV]-(27)     ##STR356##      I C.sub.3 H.sub.6 CCH,C.sub.3 H.sub.6 CCH C.sub.3 H.sub.6 CCH,C.sub.3     H.sub.6 C CH C.sub.3 H.sub.6 CCH,C.sub.3 H.sub.6 CCH C.sub.3 H.sub.6     C CH,C.sub.3 H.sub.6 CCH      [IV]-(28)     ##STR357##      SbF.sub.6 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3      H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3     H.sub.7,n-C.sub.3 H.sub.7      [IV]-(29)     ##STR358##      ClO.sub.4 C.sub.6 H.sub.4 Cl,C.sub.6 H.sub.4 Cl C.sub.6 H.sub.4     Cl,C.sub.6 H.sub.4 Cl C.sub.6 H.sub.4 Cl,C.sub.6 H.sub.4 Cl C.sub.6     H.sub.4 Cl,C.sub.6 H.sub.4 Cl      [IV]-(30)     ##STR359##      AsF.sub.6 n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3      H.sub.7,n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7,n-C.sub.3      H.sub.7  n-C.sub.3 H.sub.7,n-C.sub.3 H.sub.7      [IV]-(31)     ##STR360##      ClO.sub.4      ##STR361##      ##STR362##      ##STR363##      ##STR364##      [IV]-(32)     ##STR365##      BF.sub.4 CH.sub.3,CH.sub.3 CH.sub.3,CH.sub.3 CH.sub.3,CH.sub.3 CH.sub.3,C     H.sub.3      [IV]-(33)     ##STR366##      Br C.sub.2 H.sub.4 Cl,C.sub.2 H.sub.4 Cl C.sub.2 H.sub.4 Cl,C.sub.2     H.sub.4 Cl C.sub.2 H.sub.4 Cl,C.sub.2 H.sub.4 Cl C.sub.2 H.sub.4     Cl,C.sub.2 H.sub.4 Cl      [ IV]-(34)     ##STR367##      ClO.sub.4 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2                       C      CH.sub.2 CHC(CH.sub.3)H.sub.2 C(CH.sub.3).sub.2      CH.sub.2 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2      CH.sub.2 CHC(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2  [IV]-(35)      ##STR368##      SbF.sub.6 C.sub.2 H.sub.4 OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2     H.sub.4 OCH.sub.3,C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.5,C.sub.2     H.sub.5 C.sub.2 H.sub.5,C.sub.2 H.sub.5      [IV]-(36)     ##STR369##      ClO.sub.4 CH.sub.2 OCH.sub.3,CH.sub.2 OCH.sub.3 CH.sub.2      OCH.sub.3,CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.3     CH.sub.2 OCH.sub.3,CH.sub.2      OCH.sub.3

The infrared-absorptive compounds of the present invention, representedby formulas (III) and (IV) can be synthesized similarly to theinfrared-absorptive compounds of formulas (I) and (III) previouslydescribed, i.e., by the methods disclosed in U.S. Pat. Nos. 3,251,881,3,575,871 and 3,484,467 and Japanese Patent Application Laid-Open No.61-69991. For example, they can be synthesized according to thefollowing scheme. ##STR370## The amino compound obtained by the aboveUllmann reaction and reduction reaction is subjected to selectivesubstitution, i.e., for example, alkylation, alkenylation, aralkylationor alkynylation to substitute the hydrogen atom(s) of amino groups ofthe amino compound, followed by oxidation reaction to give the endproduct.

In this course, for example, as an alkylating agent, methyl bromide,ethyl bromide, n-propyl bromide, n-butyl bromide or the like is used,and 1,4-dibromobutane, 1,5-dibromopentane or the like is further used,whereby a heterocyclic ring can be formed together with a nitrogen atomin the combination of R'₁ and R'₂, R'₃ and R'₄, R'₅ and R'₆ or R'₇ andR'₈.

In an instance in which R'₁ to R'₈ are asymmetrically formed, theselective substitution must be multi-stepwise carried out. In view ofcost, R'₁ to R'₈ or the combinations of R'₁ and R'₂, R'₃ and R'₄, R'₅and R'₆ and R'₇ and R'₈ may preferably be the same.

The above infrared-absorptive compounds of the present invention have amaximum absorption wavelength of 900 nm or more and an absorptivitycoefficient of from several tens of thousands to hundred and severaltens of thousands, showing a great absorption peak.

Such compounds can be used, for example, in thermal insulating films,sunglasses, etc.

Next, the infrared-absorptive compound according to a third embodimentof the present invention is a compound represented by the followingformula (V) or (V). ##STR371## In formulas (V) and (VI), Z represents##STR372## and R"₁ to R"₈ each represent a hydrogen atom or a monovalentorganic residual group.

The monovalent organic residual group may include those exemplified by asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedalkenyl group, a substituted or unsubstituted aryl group, a substitutedor unsubstituted aralkyl group and also an alkynyl group. For example,the unsubstituted alkyl group may include those exemplified by a methylgroup, an ethyl group, a n-propyl group, an iso-propyl group, a n-butylgroup, an iso-butyl group, a t-buryl group, a n-amyl group, a t-amylgroup, a n-hexyl group, a n-octyl group and a t-octyl group. Thesubstituted alkyl group may include, for example, halogenated alkylgroups such as a 2-chloroethyl group and a 3-chloropropyl group,hydroxyalkyl groups such as a 2-hydroxyethyl group, a 3-hydroxypropylgroup and a 4-hydroxybutyl group, acetoxy alkyl groups such as a2-acetoxyethyl group and 2-acetoxypropyl group, carboxyalkyl groups suchas a carboxymethyl group, a 2-carboxyethyl group and a 3-carboxypropylgroup, and alkoxyalkyl groups such as a methoxymethyl group, amethoxyethyl group, a methoxypropyl group, a methoxybutyl group, anethoxymethyl group, an ethoxyethyl group, an ethoxypropyl group, anethoxybutyl group and a propoxymethyl group. The alkenyl group mayinclude those exemplified by a vinyl group, a propenyl group, a butenylgroup, a pentenyl group, a hexenyl group, a heptenyl group end anoctenyl group, end also any of these alkenyl groups whose hydrogen atomhas been substituted with a halogen atom, a hydroxyl group, an acetoxylgroup, a carboxyl group or an alkoxyl group. The aralkyl group mayinclude those exemplified by a benzyl group, a p-methylbenzyl group, a2-phenylmethyl group, a 2-phenylpropyl group, a 3-phenylpropyl group, anα-naphthylmethyl group end a β-naphthylethyl group, end also any ofthese aralkyl groups whose hydrogen atom has been substituted with ahalogen atom as exemplified by a p-chlorobenzyl group, and any of thesearalkyl groups whose hydrogen atom has been substituted with a hydroxylgroup, an acetoxyl group, a carboxyl group or an alkoxyl group. Thesubstituted or unsubstituted aryl group may include those exemplified bya phenyl group, a naphthyl group, a tolyl group, a xylyl group, amethoxyphenyl group, a dimethoxyphenyl group, a trimethoxyphenyl group,an ethoxyphenyl group, a dimethylaminophenyl group, a diethylaminophenylgroup, a dipropylaminophenyl group, a dibenzylaminophenyl group, adiphenylaminophenyl group, a dimethoxymethylaminophenyl group and aditolylaminophenyl group. The alkynyl group may include thoseexemplified by a propagyl group, a butynyl group, a pentynyl group and ahexynyl group.

R"₁ to R"₈ may be the same or may be different one another.

R"₁ to R"₈ may be in at least one combination of combinations R"₁ andR"₂, R"₃ and R"₄, R"₅ and R"₆ and R"₇ and R"₈, a group of atomsnecessary to form a substituted or unsubstituted 5-membered ring, asubstituted or unsubstituted 6-membered ring or a substituted orunsubstituted 7-membered ring together with a nitrogen atom. The5-membered ring may include, for example, a pyrrolidine ring, the6-membered ring may include a piperidine ring, a morpholine ring and 8tetrahydropyridine group, and the 7-membered ring may include thecylcohexylamine ring represented by formula (VII) previously described.Of the substituents R"₁ to R"₈ two or more of the above combinations maybe made to have the heterocyclic structure described above, and in suchan instance, the structure may be the same or different from each other.

In the above infrared-absorptive compounds of formulas (V) and (VI), atleast one of R"₁ to R"₈ or preferably all of them may be a monovalentorganic residual group having 1 to 8 carbon atoms, in particular, asubstituted or unsubstituted alkenyl group or a substituted orunsubstituted alkoxyalkyl group. In such an instance, the heatresistance of the infrared-absorptive compounds can be improved and alsothe solvent solubility thereof can be improved.

R"₉ also represents a hydrogen atom, or a monovalent organic residualgroup which may include, for example, alkyl groups as exemplified by amethyl group, an ethyl group, a n-propyl group, an iso-propyl group, an-butyl group, a sec-butyl group, an iso-butyl group, a t-butyl group, an-amyl group, a t-amyl group, a n-hexyl group, a n-octyl group and at-octyl group; substituted alkyl groups as exemplified by a2-hydroxyethyl group, a 3-hydroxypropyl group, a 4-hydroxybutyl group, a2-acetoxyethyl group, a carboxymethyl group, a 2-carboxyethyl group, a3-carboxypropyl group, a 2-sulfoethyl group, a 3-sulfopropyl group, a4-sulfobutyl group, a sulfatopropyl group, a sulfatobutyl group, anN-(methylsulfonyl)carbamylmethyl group, a 3-(acetylsulfamyl)propyl groupand a 4-(acetylsulfamyl)butyl group; cyclic alkyl groups as exemplifiedby a cylcohexyl group; alkenyl groups such as an allyl group (CH₂═CH--CH₂ --); aralkyl groups as exemplified by a benzyl group, aphenethyl group, an α-naphthylmethyl group and a β-naphthylmethyl group;substituted aralkyl groups as exemplified by a carboxybenzyl group, asulfobenzyl group and a hydroxybenzyl group; and aryl groups asexemplified by a phenyl group or substituted aryl groups as exemplifiedby a carboxyphenyl group, a sulfophenyl group and a hydroxyphenyl group.

X.sup.⊖ represents the same anionic residual group as previouslydescribed.

Examples of the infrared-absorptive compounds of formulas (V) and (VI)according to the present invention are shown below. In the presentinvention, examples are by no means limited to these.

The following exemplary compounds (V)-A-(1) to (VI)-D-(27) are set outin the manner simplified as follows:

For example, in the infrared-absorptive compounds of formulas (V) and(VI), a compound having the following structure (F) is indicated asshown below.

    __________________________________________________________________________    (F)                                                                               ##STR373##                                                                 ##STR374##                                                                              ##STR375##                                                                         ##STR376##                                                                         ##STR377##                                                                           ##STR378##                                                                            ##STR379##                                                                           ##STR380##                         __________________________________________________________________________    (F)                                                                                      ##STR381##                                                                        ClO.sub.4                                                                          CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3                                                CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3                                                 CH.sub.2 OCH.sub.3 CH.sub.2 OCH.sub.3                                                CH.sub.2 OCH.sub.3 CH.sub.2                                                   OCH.sub.3                           __________________________________________________________________________

    __________________________________________________________________________     ##STR382##                                                                             ##STR383##                                                                              ##STR384##                                                                                ##STR385##                                                                            ##STR386##                                                                            ##STR387##                                                                            ##STR388##            __________________________________________________________________________    [V]-A-(1)                                                                               ##STR389##                                                                             ClO.sub.4                                                                                  ##STR390##                                                                            ##STR391##                                                                            ##STR392##                                                                            ##STR393##            [V]-A-(2)                                                                               ##STR394##                                                                             BF.sub.4                                                                                   ##STR395##                                                                            ##STR396##                                                                            ##STR397##                                                                            ##STR398##            [V]-A-(3)                                                                               ##STR399##                                                                             SbF.sub.6                                                                                  ##STR400##                                                                            ##STR401##                                                                            ##STR402##                                                                            ##STR403##            [V]-A-(4)                                                                               ##STR404##                                                                             Br                                                                                         ##STR405##                                                                            ##STR406##                                                                            ##STR407##                                                                            ##STR408##            [V]-A-(5)                                                                               ##STR409##                                                                             ClO.sub.4                                                                                  ##STR410##                                                                            ##STR411##                                                                            ##STR412##                                                                            ##STR413##            [V]-A-(6)                                                                               ##STR414##                                                                             SbF.sub.6                                                                                  ##STR415##                                                                            ##STR416##                                                                            ##STR417##                                                                            ##STR418##            [V]-A-(7)                                                                               ##STR419##                                                                             CH.sub.3 SO.sub.4                                                                          ##STR420##                                                                            ##STR421##                                                                            ##STR422##                                                                            ##STR423##            [V]-A-(8)                                                                               ##STR424##                                                                             ClO.sub.4                                                                                  ##STR425##                                                                            ##STR426##                                                                            ##STR427##                                                                            ##STR428##            [V]-A-(9)                                                                               ##STR429##                                                                             AsF.sub.6                                                                                  ##STR430##                                                                            ##STR431##                                                                            ##STR432##                                                                            ##STR433##            [V]-A-(10)                                                                              ##STR434##                                                                             ClO.sub.4                                                                                  ##STR435##                                                                            ##STR436##                                                                            ##STR437##                                                                            ##STR438##            [V]-A-(11)                                                                              ##STR439##                                                                             Cl                                                                                         ##STR440##                                                                            ##STR441##                                                                            ##STR442##                                                                            ##STR443##            [V]-A-(12)                                                                              ##STR444##                                                                             ClO.sub.4                                                                                  ##STR445##                                                                            ##STR446##                                                                            ##STR447##                                                                            ##STR448##            [V]-A-(13)                                                                              ##STR449##                                                                             ClO.sub.4                                                                                  ##STR450##                                                                            ##STR451##                                                                            ##STR452##                                                                            ##STR453##            [V]-A-(14)                                                                              ##STR454##                                                                             SbF.sub.6                                                                                  ##STR455##                                                                            ##STR456##                                                                            ##STR457##                                                                            ##STR458##            [V]-A-(15)                                                                              ##STR459##                                                                              ##STR460##                                                                                ##STR461##                                                                            ##STR462##                                                                            ##STR463##                                                                            ##STR464##            [V]-A-(16)                                                                              ##STR465##                                                                             ClO.sub.4                                                                                  ##STR466##                                                                            ##STR467##                                                                            ##STR468##                                                                            ##STR469##            [V]-A-(17)                                                                              ##STR470##                                                                             I                                                                                          ##STR471##                                                                            ##STR472##                                                                            ##STR473##                                                                            ##STR474##            [V]-A-(18)                                                                              ##STR475##                                                                             ClO.sub.4                                                                                  ##STR476##                                                                            ##STR477##                                                                            ##STR478##                                                                            ##STR479##            [V]-A-(19)                                                                              ##STR480##                                                                             Br                                                                                         ##STR481##                                                                            ##STR482##                                                                            ##STR483##                                                                            ##STR484##            [V]-A-(20)                                                                              ##STR485##                                                                             ClO.sub.4                                                                                  ##STR486##                                                                            ##STR487##                                                                            ##STR488##                                                                            ##STR489##            [V]-A-(21)                                                                              ##STR490##                                                                             I                                                                                          ##STR491##                                                                            ##STR492##                                                                            ##STR493##                                                                            ##STR494##            [V]-A-(22)                                                                              ##STR495##                                                                             SbF.sub.6                                                                                  ##STR496##                                                                            ##STR497##                                                                            ##STR498##                                                                            ##STR499##            [V]-A-(23)                                                                              ##STR500##                                                                             ClO.sub.4                                                                                  ##STR501##                                                                            ##STR502##                                                                            ##STR503##                                                                            ##STR504##            [V]-A-(24)                                                                              ##STR505##                                                                             AsF.sub.6                                                                                  ##STR506##                                                                            ##STR507##                                                                            ##STR508##                                                                            ##STR509##            [V]-A-(25)                                                                              ##STR510##                                                                             BF.sub.4                                                                                   ##STR511##                                                                            ##STR512##                                                                            ##STR513##                                                                            ##STR514##            [V]-A-(26)                                                                              ##STR515##                                                                             Br                                                                                         ##STR516##                                                                            ##STR517##                                                                            ##STR518##                                                                            ##STR519##            [V]-A-(27)                                                                              ##STR520##                                                                             SbF.sub.6                                                                                  ##STR521##                                                                            ##STR522##                                                                            ##STR523##                                                                            ##STR524##            [V]-B-(1)                                                                               ##STR525##                                                                             ClO.sub.4                                                                                  ##STR526##                                                                            ##STR527##                                                                            ##STR528##                                                                            ##STR529##            [V]-B-(2)                                                                               ##STR530##                                                                             BF.sub.4                                                                                   ##STR531##                                                                            ##STR532##                                                                            ##STR533##                                                                            ##STR534##            [V]-B-(3)                                                                               ##STR535##                                                                             SbF.sub.6                                                                                  ##STR536##                                                                            ##STR537##                                                                            ##STR538##                                                                            ##STR539##            [V]-B-(4)                                                                               ##STR540##                                                                             Br                                                                                         ##STR541##                                                                            ##STR542##                                                                            ##STR543##                                                                            ##STR544##            [V]-B-(5)                                                                               ##STR545##                                                                             ClO.sub.4                                                                                  ##STR546##                                                                            ##STR547##                                                                            ##STR548##                                                                            ##STR549##            [V]-B-(6)                                                                               ##STR550##                                                                             SbF.sub.6                                                                                  ##STR551##                                                                            ##STR552##                                                                            ##STR553##                                                                            ##STR554##            [V]-B-(7)                                                                               ##STR555##                                                                             CH.sub.3 SO.sub.4                                                                          ##STR556##                   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                                                              ##STR1219##                                                                           ##STR1220##                                                                           ##STR1221##                                                                           ##STR1222##           [VI]-B-(26)                                                                             ##STR1223##                                                                            Br                                                                                         ##STR1224##                                                                           ##STR1225##                                                                           ##STR1226##                                                                           ##STR1227##           [VI]-B-(27)                                                                             ##STR1228##                                                                            SbF.sub.6                                                                                  ##STR1229##                                                                           ##STR1230##                                                                           ##STR1231##                                                                           ##STR1232##           __________________________________________________________________________

    __________________________________________________________________________     ##STR1233##                                                                            ##STR1234##                                                                        ##STR1235##                                                                                ##STR1236##                                                                            ##STR1237##                                                                            ##STR1238##                                                                            ##STR1239##            __________________________________________________________________________    [VI]-C-(1)                                                                              ##STR1240##                                                                       ClO.sub.4    CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.3                                                 CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.3                                                 CH.sub.2 OCH.sub.3, CH.sub.2                                                  OCH.sub.3                                                                              CH.sub.2 OCH.sub.3,                                                           H.sub.2 OCH.sub.3       [VI]-C-(2)                                                                              ##STR1241##                                                                       BF.sub.4     C.sub.2 H.sub.5, C.sub.2 H.sub.5                                                       C.sub.2 H.sub.5, C.sub.2 H.sub.                                                        C.sub.2 H.sub.5, C.sub.2                                                      H.sub.5  C.sub.2 H.sub.5,                                                              C.sub.2 H.sub.5         [VI]-C-(3)                                                                              ##STR1242##                                                                       SbF.sub.6    C.sub.2 H.sub.5, C.sub.2 H.sub.5                                                       C.sub.2 H.sub.5, C.sub.2 H.sub.5                                                       C.sub.2 H.sub.5, C.sub.2                                                      H.sub.5  C.sub.2 H.sub.5,                                                              C.sub.2 H.sub.5         [VI]-C-(4)                                                                              ##STR1243##                                                                       Br                                                                                          ##STR1244##                                                                            ##STR1245##                                                                            ##STR1246##                                                                            ##STR1247##            [VI]-C-(5)                                                                              ##STR1248##                                                                       ClO.sub.4    n-C.sub.3 H.sub.7, n-C.sub.3                                                           n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3                                                  H.sub.7  n-C.sub.3 H.sub.7,                                                            n-C.sub.3 H.sub.7       [VI]-C-(6)                                                                              ##STR1249##                                                                       SbF.sub.6    iso-C.sub.3 H.sub.7, iso-C.sub.3 H.sub.7                                               iso-C.sub.3 H.sub.7, iso-C.sub.3                                              H.sub.7  iso-C.sub.3 H.sub.7,                                                          iso-C.sub.3 H.sub.7                                                                    iso-C.sub.3                                                                   H.sub.7, iso-C.sub.3                                                           H.sub.7                [VI]-C-(7)                                                                              ##STR1250##                                                                       CH.sub.3 SO.sub.4                                                                          C.sub.3 H.sub.6 OC.sub.3 H.sub.7, C.sub.3                                     H.sub.6 OC.sub.3 H.sub.7                                                               C.sub.3 H.sub.6 OC.sub.3 H.sub.7,                                             C.sub.3 H.sub.6 OC.sub.3 H.sub.7                                                       C.sub.3 H.sub.6 OC.sub.3                                                      H.sub.7, C.sub.3 H.sub.6                                                      OC.sub.3 H.sub.7                                                                       C.sub.3 H.sub.6                                                               OC.sub.3 H.sub.7,                                                             C.sub.3 H.sub.6                                                               OC.sub.3 H.sub.7        [VI]-C-(8)                                                                              ##STR1251##                                                                       ClO.sub.4    CH.sub.2 CHCH.sub.2, CH.sub.2                                                          CH.sub.2 CHCH.sub.2, CH.sub.2                                                 CHCH.sub.2                                                                             CH.sub.2 CHCH.sub.2,                                                          CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2,                                                           CH.sub.2 CHCH.sub.2                                                          8                       [VI]-C-(9)                                                                              ##STR1252##                                                                       AsF.sub.6    C.sub.2 H.sub.4 CHCH.sub.2, C.sub.2 H.sub.4                                   CHCH.sub.2                                                                             C.sub.2 H.sub.4 CHCH.sub.2, C.sub.2                                           H.sub.4 CHCH.sub.2                                                                     C.sub.2 H.sub.4 CHCH.sub.2,                                                   C.sub.2 H.sub.4 CHCH.sub.2                                                             C.sub.2 H.sub.4                                                               CHCH.sub.2, C.sub.2                                                           H.sub.4 CHCH.sub.2      [VI]-C-(10)                                                                             ##STR1253##                                                                       ClO.sub.4    n-C.sub.4 H.sub.9, n-C.sub.4 H.sub.9                                                   n-C.sub.4 H.sub.9, n-C.sub.4 H.sub.9                                                   n-C.sub.4 H.sub.9, n-C.sub.4                                                  H.sub.9  n-C.sub.4 H.sub.9,                                                            n-C.sub.4 H.sub.9       [VI]-C-(11)                                                                             ##STR1254##                                                                       Cl           n-C.sub.10 H.sub.21, n-C.sub.10 H.sub.21                                               n-C.sub.10 H.sub.21, n-C.sub.10                                               H.sub.21 n-C.sub.10 H.sub.21,                                                          n-C.sub.10 H.sub.21                                                                    n-C.sub.10 H.sub.21,                                                           n-C.sub.10                                                                   H.sub.21                [VI]-C-(12)                                                                             ##STR1255##                                                                       ClO.sub.4    C.sub.2 H.sub.4 CHCH.sub.2, C.sub.2 H.sub.4                                   CHCH.sub.2                                                                             C.sub.2 H.sub.4 CHCH.sub.2, C.sub.2                                           H.sub.4 CHCH.sub.2                                                                     C.sub.2 H.sub.4 CHCH.sub.2,                                                   C.sub.2 H.sub.4 CHCH.sub.2                                                             C.sub.2 H.sub.4                                                               CHCH.sub.2, C.sub.2                                                           H.sub.4 CHCH.sub.2      [VI]-C-(13)                                                                             ##STR1256##                                                                       ClO.sub.4    C.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.2                                     H.sub.4 OC.sub.2 H.sub.5                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.5,                                             C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                       C.sub.2 H.sub.4 OC.sub.2                                                      H.sub.5, C.sub.2 H.sub.4                                                      OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.4                                                               OC.sub.2 H.sub.5,                                                             C.sub.2 H.sub.4                                                               OC.sub.2 H.sub.5        [VI]-C-(14)                                                                             ##STR1257##                                                                       SbF.sub.6    C.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4                                    OCH.sub.3                                                                              C.sub.2 H.sub.4 OCH.sub.3, C.sub.2                                            H.sub.4 OCH.sub.3                                                                      C.sub.2 H.sub.4 OCH.sub.3,                                                    C.sub.2 H.sub.4 OCH.sub.3                                                              C.sub.2 H.sub.4                                                               OCH.sub.3, C.sub.2                                                            H.sub.4 OCH.sub.3       [VI-C-(15)                                                                              ##STR1258##                                                                        ##STR1259## n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.4 H.sub.9, n-C.sub.4 H.sub.9                                                   n-C.sub.3 H.sub.7, n-C.sub.3                                                  H.sub.7  n-C.sub.4 H.sub.9,                                                            n-C.sub.4 H.sub.9       [VI]-C-(16)                                                                             ##STR1260##                                                                       ClO.sub.4    n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.5 H.sub.11, n-C.sub.5                                                  H.sub.11                                                                              n-C.sub.5 H.sub.11,                                                           -C.sub.5 H.sub.11       [VI]-C-(17)                                                                             ##STR1261##                                                                       I            C.sub. 3 H.sub.7 OH, C.sub.3 H.sub.7 OH                                                C.sub.3 H.sub.7 OH, C.sub.3 H.sub.7                                           OH       C.sub.3 H.sub.7 OH, C.sub.3                                                   H.sub.7 OH                                                                             C.sub.3 H.sub.7 OH,                                                           .sub.3 H.sub.7 OH       [VI]-C-(18)                                                                             ##STR1262##                                                                       ClO.sub.4    C.sub.2 H.sub.5, C.sub.3 H.sub.7                                                       C.sub.2 H.sub.5, C.sub.3 H.sub.7                                                       C.sub.2 H.sub.5, C.sub.3                                                      H.sub.7  C.sub.2 H.sub.5,                                                              C.sub.3 H.sub.7         [VI]-C-(19)                                                                             ##STR1263##                                                                       Br                                                                                          ##STR1264##                                                                           n-C.sub.5 H.sub.11, n-C.sub.5                                                 H.sub.11 n-C.sub.5 H.sub.11, n-C.sub.5                                                  H.sub.11                                                                              n-C.sub.5 H.sub.11,                                                           -C.sub.5 H.sub.11       [VI]-C-(20)                                                                             ##STR1265##                                                                       ClO.sub.4    C.sub.2 H.sub.4 CCH, C.sub. 2 H.sub.4 CCH                                              C.sub.2 H.sub.4 CCH, C.sub.2 H.sub.4                                          C CH     C.sub.2 H.sub.4 CCH, C.sub.2                                                  H.sub.4 CCH                                                                            C.sub.2 H.sub.4                                                               CCH, C.sub.2                                                                  H.sub.4 CCH             [VI]-C-(21)                                                                             ##STR1266##                                                                       I            C.sub.3 H.sub.6 CCH, C.sub.3 H.sub.6 CCH                                               C.sub.3 H.sub.6 CCH, C.sub.3 H.sub.6                                          C CH     C.sub.3 H.sub.6 C CH,                                                         C.sub.3 H.sub.6 CCH                                                                    C.sub.3 H.sub.6                                                               CCH, C.sub.3                                                                  H.sub.6 CCH             [VI]-C-(22)                                                                             ##STR1267##                                                                       SbF.sub.6    n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3                                                  H.sub.7  n-C.sub.3 H.sub.7,                                                            n-C.sub.3 H.sub.7       [VI]-C-(23)                                                                             ##STR1268##                                                                       ClO.sub.4    C.sub.6 H.sub.4 Cl, C.sub.6 H.sub.4 Cl                                                 C.sub.6 H.sub.4 Cl, C.sub.6 H.sub.4                                           Cl       C.sub.6 H.sub.4 Cl, C.sub.6                                                   H.sub.4 Cl                                                                             C.sub.6 H.sub.4 Cl,                                                           .sub.6 H.sub.4 Cl       [VI]-C-(24)                                                                             ##STR1269##                                                                       AsF.sub.6    n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3                                                  H.sub.7  n-C.sub.3 H.sub.7,                                                            n-C.sub.3 H.sub.7       [VI]-C-(25)                                                                             ##STR1270##                                                                       BF.sub.4     CH.sub.3, CH.sub.3                                                                     CH.sub.3, CH.sub.3                                                                     CH.sub.3, CH.sub.3                                                                     CH.sub.3, CH.sub.3      [VI]-C-(26)                                                                             ##STR1271##                                                                       Br           C.sub.2 H.sub.4 Cl, C.sub.2 H.sub.4 Cl                                                 C.sub.2 H.sub.4 Cl, C.sub.2 H.sub.4                                           Cl       C.sub.2 H.sub.4 Cl, C.sub.2                                                   H.sub.4 Cl                                                                             C.sub.2 H.sub.4 Cl,                                                           .sub.2 H.sub.4 Cl       [VI]-C-(27)                                                                             ##STR1272##                                                                       SbF.sub.6    C.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4                                    OCH.sub.3                                                                              C.sub.2 H.sub.4 OCH.sub.3, C.sub.2                                            H.sub.4 OCH.sub.3                                                                      C.sub.2 H.sub.5, C.sub.2                                                      H.sub.5  C.sub.2 H.sub.5,                                                              C.sub.2 H.sub.5         __________________________________________________________________________

    __________________________________________________________________________     ##STR1273##                                                                            ##STR1274##                                                                        ##STR1275##                                                                                ##STR1276##                                                                            ##STR1277##                                                                            ##STR1278##                                                                            ##STR1279##            __________________________________________________________________________    [VI]-D-(1)                                                                              ##STR1280##                                                                       ClO.sub.4    CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.3                                                 CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.3                                        N        CH.sub.2 OCH.sub.3, CH.sub.2                                                  OCH.sub.3                                                                              CH.sub.2 OCH.sub.3,                                                           H.sub.2 OCH.sub.3       [VI]-D-(2)                                                                              ##STR1281##                                                                       BF.sub.4     C.sub.2 H.sub.5, C.sub.2 H.sub.5                                                       C.sub.2 H.sub.5, C.sub.2 H.sub.                                                        C.sub.2 H.sub.5, C.sub.2                                                      H.sub.5  C.sub.2 H.sub.5,                                                              C.sub.2 H.sub.5         [VI]-D-(3)                                                                              ##STR1282##                                                                       SbF.sub.6    C.sub.2 H.sub.5, C.sub.2 H.sub.5                                                       C.sub.2 H.sub.5, C.sub.2 H.sub.5                                                       C.sub.2 H.sub.5, C.sub.2                                                      H.sub.5  C.sub.2 H.sub.5,                                                              C.sub.2 H.sub.5         [VI]-D-(4)                                                                              ##STR1283##                                                                       Br                                                                                          ##STR1284##                                                                            ##STR1285##                                                                            ##STR1286##                                                                            ##STR1287##            [VI]-D-(5)                                                                              ##STR1288##                                                                       ClO.sub.4    n-C.sub.3 H.sub.7, n-C.sub.3                                                           n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3                                                  H.sub.7  n-C.sub.3 H.sub.7,                                                            n-C.sub.3 H.sub.7       [VI]-D-(6)                                                                              ##STR1289##                                                                       SbF.sub.6    iso-C.sub.3 H.sub.7, iso-C.sub.3 H.sub.7                                               iso-C.sub.3 H.sub.7, iso-C.sub.3                                              H.sub.7  iso-C.sub.3 H.sub.7,                                                          iso-C.sub.3 H.sub.7                                                                    iso-C.sub.3                                                                   H.sub.7, iso-C.sub.3                                                           H.sub.7                [VI]-D-(7)                                                                              ##STR1290##                                                                       CH.sub.3 SO.sub.4                                                                          C.sub.3 H.sub.6 OC.sub.3 H.sub.7, C.sub.3                                     H.sub.6 OC.sub.3 H.sub.7                                                               C.sub.3 H.sub.6 OC.sub.3 H.sub.7,                                             C.sub.3 H.sub.6 OC.sub.3 H.sub.7                                                       C.sub.3 H.sub.6 OC.sub.3                                                      H.sub.7, C.sub.3 H.sub.6                                                      OC.sub.3 H.sub.7                                                                       C.sub.3 H.sub.6                                                               OC.sub.3 H.sub.7,                                                             C.sub.3 H.sub.6                                                               OC.sub.3 H.sub.7        [VI]-D-(8)                                                                              ##STR1291##                                                                       ClO.sub.4    CH.sub.2 CHCH.sub.2, CH.sub.2                                                          CH.sub.2 CHCH.sub.2, CH.sub.2                                                 CHCH.sub.2                                                                             CH.sub.2 CHCH.sub.2,                                                          CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2,                                                           CH.sub.2 CHCH.sub.2    [VI]-D-(9)                                                                              ##STR1292##                                                                       AsF.sub.6    C.sub.2 H.sub.4 CHCH.sub.2, C.sub.2 H.sub.4                                   CHCH.sub.2                                                                             C.sub.2 H.sub.4 CHCH.sub.2, C.sub.2                                           H.sub.4 CHCH.sub.2                                                                     C.sub.2 H.sub.4 CHCH.sub.2,                                                   C.sub.2 H.sub.4 CHCH.sub.2                                                             C.sub.2 H.sub.4                                                               CHCH.sub.2, C.sub.2                                                           H.sub.4 CHCH.sub.2      [VI]-D-(10)                                                                             ##STR1293##                                                                       ClO.sub.4    n-C.sub.4 H.sub.9, n-C.sub.4 H.sub.9                                                   n-C.sub.4 H.sub.9, n-C.sub.4 H.sub.9                                                   n-C.sub.4 H.sub.9, n-C.sub.4                                                  H.sub.9  n-C.sub.4 H.sub.9,                                                            n-C.sub.4 H.sub.9       [VI]-D-(11)                                                                             ##STR1294##                                                                       Cl           n-C.sub.10 H.sub.21, n-C.sub.10 H.sub.21                                               n-C.sub.10 H.sub.21, n-C.sub.10                                               H.sub.21 n-C.sub.10 H.sub.21,                                                          n-C.sub.10 H.sub.21                                                                    n-C.sub.10 H.sub.21,                                                           n-C.sub.10                                                                   H.sub.21                [VI]-D-(12)                                                                             ##STR1295##                                                                       ClO.sub.4    C.sub.2 H.sub.4 CHCH.sub.2, C.sub.2 H.sub.4                                   CHCH.sub.2                                                                             C.sub.2 H.sub.4 CHCH.sub.2, C.sub.2                                           H.sub.4 CHCH.sub.2                                                                     C.sub.2 H.sub.4 CHCH.sub.2,                                                   C.sub.2 H.sub.4 CHCH.sub.2                                                             C.sub.2 H.sub.4                                                               CHCH.sub.2, C.sub.2                                                           H.sub.4 CHCH.sub.2      [VI]-D-(13)                                                                             ##STR1296##                                                                       ClO.sub.4    C.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.2                                     H.sub.4 OC.sub.2 H.sub.5                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.5,                                             C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                       C.sub.2 H.sub.4 OC.sub.2                                                      H.sub.5, C.sub.2 H.sub.4                                                      OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.4                                                               OC.sub.2 H.sub.5,                                                             C.sub.2 H.sub.4                                                               OC.sub.2 H.sub.5        [VI]-D-(14)                                                                             ##STR1297##                                                                       SbF.sub.6    C.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4                                    OCH.sub.3                                                                              C.sub.2 H.sub.4 OCH.sub.3, C.sub.2                                            H.sub.4 OCH.sub.3                                                                      C.sub.2 H.sub.4 OCH.sub.3,                                                    C.sub.2 H.sub.4 OCH.sub.3                                                              C.sub.2 H.sub.4                                                               OCH.sub.3, C.sub.2                                                            H.sub.4 OCH.sub.3       [VI]-D-(15)                                                                             ##STR1298##                                                                        ##STR1299## n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.4 H.sub.9, n-C.sub.4 H.sub.9                                                   n-C.sub.3 H.sub.7, n-C.sub.3                                                  H.sub.7  n-C.sub.4 H.sub.9,                                                            n-C.sub.4 H.sub.9       [VI]-D-(16)                                                                             ##STR1300##                                                                       ClO.sub.4    n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.5 H.sub.11, n-C.sub.5                                                  H.sub.11                                                                              n-C.sub.5 H.sub.11,                                                           -C.sub.5 H.sub.11       [VI]-D-(17)                                                                             ##STR1301##                                                                       I             C.sub.3 H.sub.7 OH, C.sub.3 H.sub.7 OH                                                C.sub.3 H.sub.7 OH, C.sub.3 H.sub.7                                           OH       C.sub.3 H.sub.7 OH, C.sub.3                                                   H.sub.7 OH                                                                             C.sub.3 H.sub.7 OH,                                                           .sub.3 H.sub.7 OH       [VI]-D-(18)                                                                             ##STR1302##                                                                       ClO.sub.4    C.sub.2 H.sub.5, C.sub.3 H.sub.7                                                       C.sub.2 H.sub.5, C.sub.3 H.sub.7                                                       C.sub.2 H.sub.5, C.sub.3                                                      H.sub.7  C.sub.2 H.sub.5,                                                              C.sub.3 H.sub.7         [VI]-D-(19)                                                                             ##STR1303##                                                                       Br                                                                                          ##STR1304##                                                                           n-C.sub.5 H.sub.11, n-C.sub.5                                                 H.sub.11 n-C.sub.5 H.sub.11, n-C.sub.5                                                  H.sub.11                                                                              n-C.sub.5 H.sub.11,                                                           -C.sub.5 H.sub.11       [VI]-D-(20)                                                                             ##STR1305##                                                                       ClO.sub.4    C.sub.2 H.sub.4 CCH,  C.sub.2 H.sub.4 CCH                                              C.sub.2 H.sub.4 CCH, C.sub.2 H.sub.4                                          C CH     C.sub.2 H.sub.4 CCH, C.sub.2                                                  H.sub.4 CCH                                                                            C.sub.2 H.sub.4                                                               CCH, C.sub.2                                                                  H.sub.4 CCH             [VI]-D-(21)                                                                             ##STR1306##                                                                       I            C.sub.3 H.sub.6 CCH, C.sub.3 H.sub.6 CCH                                               C.sub.3 H.sub.6 CCH C.sub.3 H.sub.6 C                                         H        C.sub.3 H.sub.6 C CH C.sub.3                                                  H.sub.6 CCH                                                                            C.sub.3 H.sub.6 CCH                                                           .sub.3 H.sub.6 CCH      [VI]-D-(22)                                                                             ##STR1307##                                                                       SbF.sub.6    n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3                                                  H.sub.7  n-C.sub.3 H.sub.7,                                                            n-C.sub.3 H.sub.7       [VI]-D-(23)                                                                             ##STR1308##                                                                       ClO.sub.4    C.sub.6 H.sub.4 Cl, C.sub.6 H.sub.4 Cl                                                 C.sub.6 H.sub.4 Cl, C.sub.6 H.sub.4                                           Cl       C.sub.6 H.sub.4 Cl, C.sub.6                                                   H.sub.4 Cl                                                                             C.sub.6 H.sub.4 Cl,                                                           .sub.6 H.sub.4 Cl       [VI]-D-(24)                                                                             ##STR1309##                                                                       AsF.sub.6    n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub.3 H.sub.7, n-C.sub.3 H.sub.7                                                   n-C.sub. 3 H.sub.7, n-C.sub.3                                                  H.sub.7 n-C.sub.3 H.sub.7,                                                            n-C.sub.3 H.sub.7       [VI]-D-(25)                                                                             ##STR1310##                                                                       BF.sub.4     CH.sub.3, CH.sub.3                                                                     CH.sub.3, CH.sub.3                                                                     CH.sub.3, CH.sub.3                                                                     CH.sub.3, CH.sub.3      [VI]-D-(26)                                                                             ##STR1311##                                                                       Br           C.sub.2 H.sub.4 Cl, C.sub.2 H.sub.4 Cl                                                 C.sub.2 H.sub.4 Cl, C.sub.2 H.sub.4                                           Cl       C.sub.2 H.sub.4 Cl, C.sub.2                                                   H.sub.4 Cl                                                                             C.sub.2 H.sub.4 Cl,                                                           .sub.2 H.sub.4 Cl       [VI]-D-(27)                                                                             ##STR1312##                                                                       SbF.sub.6    C.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4                                    OCH.sub.3                                                                              C.sub.2 H.sub.4 OCH.sub.3, C.sub.2                                            H.sub.4 OCH.sub.3                                                                      C.sub.2 H.sub.5, C.sub.2                                                      H.sub.5  C.sub.2 H.sub.5,                                                              C.sub.2 H.sub.5         __________________________________________________________________________

The infrared-absorptive compounds of the present invention, representedby formulas (V) and (VI) can be synthesized, as previously described, bythe methods disclosed in U.S. Pat. Nos. 3,251,881, 3,575,871 and3,484,467 and Japanese Patent Application Laid-Open No. 61-69991. Forexample, they can be synthesized according to the following scheme.##STR1313## The amino compound obtained by the above Ullmann reactionand reduction reaction is subjected to selective substitution, i.e., forexample, alkylation, alkoxyalkylation, alkenylation, aralkylation oralkynylation to substitute the hydrogen atom(s) of amino groups of theamino compound, followed by silver salt oxidation or electrolyticoxidation reaction to give the end product.

In an instance in which R"₁ to R"₈ are asymmetrically formed, theselective substitution must be multi-stepwise carried out. In view ofcost R"₁ to R"₈ may preferably be the same.

The above infrared-absorptive compounds of the present invention have amaximum absorption wavelength of 900 nm or more and an absorptivitycoefficient of from several tens of thousands to hundred and severaltens of thousands, showing a great absorption peak.

Such compounds can be used, for example, in thermal insulating films,sunglasses, etc.

The infrared-absorptive compounds represented by formulas (I), (II),(III), (IV), (V) and (VI) described above are very effective for theirincorporation into recording layers containing organic coloring matterof optical recording mediums. More specifically, incorporation of theinfrared-absorptive compound of the present invention into an organiccoloring matter recording layer of optical recording mediums makes itpossible to prevent recording-reproducing performance (e.g., C/N ratioand contrast ratio) from being lowered because of irradiation of opticalrecording mediums with natural light or reproducing light, and alsomakes it possible to very greatly prevent recording-reproducingperformance of optical recording mediums from being lowered in anenvironment of high temperature compared with optical recording mediumshaving organic coloring matter recording layers containing anyconventional infrared-absorptive compounds.

The infrared-absorptive compounds represented by formulas (I) to (VI) ofthe present invention show a good solvent solubility, and it becomespossible to improve productivity of a high-quality optical recordingmedium without causing an increase in noise level of optical recordingmediums, even when the organic coloring matter recording layers areformed by wet coating.

In the optical recording medium according to the present invention, theorganic coloring matter incorporated into the recording layer togetherwith the infrared-absorptive compound of the present invention mayinclude commonly available organic coloring matters usable in opticalrecording mediums, as exemplified by cyanine dyes, merocyanine dyes,croconium dyes, squalium dyes, azlenium dyes, polymethine dyes,naphthoquinone dyes, pyrylium dyes and phthalocyanine dyes, specificallyincluding, for example, polymethine dyes disclosed in U.S. Pat. No.5,079,127, represented by the following formula (VIII), and cyanine dyesdisclosed in Japanese Patent Application Laid-open No. 1-21798,represented by the following formula (IX). ##STR1314## wherein, A', B',D' and E' each represent a hydrogen atom or a group selected from asubstituted or unsubstituted alkyl group-, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted aralkylgroup, a substituted or unsubstituted aryl group, a substituted orunsubstituted styryl group and a substituted or unsubstitutedheterocyclic group; r₁ ' and r₂ ' each represent a hydrogen atom or agroup selected from a substituted or unsubstituted alkyl group, asubstituted or unsubstituted cyclic alkyl group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted aralkylgroup and a substituted or unsubstituted aryl group; k is 0 or 1 and 1is 0, 1 or 2; and G.sup.⊖ represents an anionic residual group.##STR1315## wherein "J" represents a group of non-metal atoms necessaryto complete a nitrogen-containing heterocyclic ring; r₁ ' to r₇ ' areeach as defined for r₁ ' and r₂ ' previously; t is 0 or 1, k is 0 or 1and 1 is 0, 1 or 2; and G.sup.⊖ represents an anionic residual group.

In the optical recording medium according to the present invention, theinfrared-absorptive compound of the present invention may suitably beadded in the recording layer in an amount of from 1 to 60% by weight,preferably from 5 to 40% by weight, and more preferably from 10 to 30%by weight, based on the whole solid content of the recording layer.

The optical recording medium of the present invention can be formed byproviding as shown in FIG. 1 a recording layer 2 on a substrate 1.

As materials for the substrate 1, it is possible to use plastics ofpolyesters, polycarbonates, acrylic resins, polyolefin resins, phenolresins, epoxy resins, polyamides, polyimides or the like, glasses, ormetals.

Incidentally, the recording layer 2 can be formed on the substrate 1 byvarious methods including wet coating and gaseous phase deposition suchas vacuum deposition. In particular, the wet coating is a preferablemethod in view of the reduction of production cost of the opticalrecording medium.

In the case when the wet coating is used, the recording layer can beformed by coating on the substrate 1 a solution prepared by dissolvingor dispersing the polymethine compound (the infrared-absorptivecompound) in an organic solvent. If necessary, the recording layer canalso be formed by mixing a binder in it, taking account of film formingproperties and coating film stability.

The organic solvent that can be used in the wet coating may varydepending on whether the polymethine compound is dispersed or dissolved.In usual instances, solvents of an alcohol type, a ketone type, an amidetype, an ether type, an ester type, an aliphatic halogenated hydrocarbontype, an aromatic type, an aliphatic hydrocarbon type or a fluorine typecan be used. In particular, solvents capable of well dissolving thepolymethine compound of the present invention are preferred.

Meanwhile, in the case when the wet coating is directly carried out on aresin substrate, an organic solvent that does not dissolve the surfaceof the resin substrate or may cause no cracking on the surface of theresin substrate must be selected from among the organic solventsdescribed above.

Since, however, the infrared-absorptive compound according to thepresent invention has a superior solvent solubility, the solvents forcoating or materials for the substrate can be selected in a wider rangethan in conventional cases even when an organic coloring matter solutionis coated by wet coating and also the conditions for producing excellentoptical recording mediums with a low noise level can be moderated thanin conventional cases.

The binder mentioned above may include, for example, nitrocellulose,ethyl cellulose, polystyrene, polyvinyl pyrrolidone, polymethylmethacrylate and polyamide. Waxes, higher fatty acids and amides asexemplified by oleylamide may also optionally be used as additives.

In the above binder, a plasticizer such as dioctyl phthalate, dibutylphthalate or tricresyl phosphate, an oil such as mineral oil orvegetable oil and also a dispersing agent such as a sodiumalkylbenzenesulfonate or a polyoxyethylene alkylphenyl ether, as well asother additives may be appropriately mixed so that the film formingproperties and coating film stability of the recording layer can beimproved.

The coating can be carried out using a coating process such as dipcoating, spray coating, spin coating, bead coating, wire bar coating,blade coating, curtain coating, roller coating or gravure coating.

It is suitable for the recording layer to have a layer thickness of from100 Å to 20 μm, and preferably from 200 Å to 1 μm. It is better for thelayer to be as thin as possible so long as a thin film having asufficient light-reflectance to recording laser light can be stablyformed.

As shown in FIG. 2, the optical recording medium of the presentinvention may also be provided on the recording layer 2, with aprotective layer 3 that is transparent to recording-reproducing laserlight. The protective layer 3 may be opaque when irradiated with lightfrom the substrate 1 side.

As shown in FIG. 3, a subbing layer 4 may also be provided between thesubstrate 1 and the recording layer 2.

As shown in FIG. 4, it is also possible to form the protective layer andthe subbing layer 4 together.

The subbing layer 3 is provided for the purposes of (a) improvingadhesion, (b) serving as a barrier to water or gas, (c) improvingstorage stability of the recording layer, (d) improving reflectance, (e)protecting the substrate from solvents and (f) forming pregrooves. Forthe purpose (a), polymeric materials can be used, as exemplified byvarious materials such as ionomer resins, polyamide resins, vinylresins, natural polymers, silicone end liquid rubbers, or varioussubstances such as silane coupling agents. For the purposes (b) end (c),besides the above polymeric materials, it is possible to use inorganiccompounds as exemplified by SiO₂, MgF₂,SiO, TiO₂, ZnO, TiN and SiN, andmetals or semimetals as exemplified by Zn, Cu, S, Ni, Cr, Ge, Se, Cd, Agand Al. For the purpose (d), metals as exemplified by Al end Ag, ormaterials capable of forming organic thin films having a metallic gloss,as exemplified by eyenine dyes and methine dyes can be used. For thepurposes (e) and (f), ultraviolet-curable resins, thermosetting resinsand thermoplastic resins can be used. It is suitable for the subbinglayer to have a layer thickness of from 50 Å to 100 μm and preferablyfrom 200 Å to 30 μm.

The protective layer is provided for the purposes of protecting therecording layer from scratches, dust, soil, etc. and improving storagestability and reflectance of the recording layer. As materials therefor,the same materials as those for the subbing layer can be used. It issuitable for the protective layer to have a layer thickness of 100 Å ormore, and preferably 1,000 Å or more.

Here, the subbing layer and/or the protective layer may contain(s) thepolymethine compound of formula (I) of the present invention. Thesubbing layer or the protective layer may also contain a stabilizer, adispersing agent, a flame retardant, a lubricant, an antistatic agent, asurface active agent, a plasticizer and so forth.

The optical recording medium of the present invention may also bedifferently constructed to have what is called the air-sandwichstructure wherein two recording mediums having the same construction asshown in FIGS. 1 to 4 (one of them being comprised of only the substrateas occasion calls) are so sealed as for the recording layer(s) 2 is/areprovided in the inside, or to have what is called the joined structure(laminated structure) wherein two recording mediums are bonded throughthe protective layer 3.

The optical recording medium of the present invention, produced in thisway (a record blank in which no information has been recorded) isirradiated with modulated recording electromagnetic radiations to causedecoloration or color changes or produce depressions (or pits), therebygiving an information record in which information has been recorded.

In particular, in the optical recording medium of the present invention,the information can be recorded by irradiation with light of a gas lasersuch as a helium-neon laser (oscillation wavelength: 633 nm). What issuited therefor is a method in which a record is made by irradiationwith beams of a laser having an oscillation wavelength in the nearinfrared or infrared region, e.g., preferably a laser having awavelength of 750 nm or more, in particular, a gallium-aluminum-arsenicsemiconductor laser (oscillation wavelength: 830 nm), to formdepressions in the recording layer. In order to read out theinformation, the above laser beams, having been adjusted to an intensitythat may cause no changes in the recording layer, may be used. Here, thewriting and the read-out can be performed using a laser having the samewavelength, or may be performed using lasers having differentwavelengths.

As described above, the present invention has the following advantages.

(1) An infrared-absorptive compound very stable even in an environmentof high temperature can be obtained.

(2) An infrared-absorptive compound having a superior heat resistanceand also exhibiting a good solvent solubility can be obtained.

(3) An optical recording medium more improved in storage stability in anenvironment of high temperature and also having a superiorlight-resistance stability can be obtained.

(4) A high-quality optical recording medium having superior storagestability and light-resistance stability in an environment of hightemperature and also promising a low noise level during reproduction canbe produced in a good productivity.

EXAMPLES

The present invention will be described below in greater detail bygiving Examples. In the following, "part(s)" refers to "part(s) byweight".

Synthesis Example 1

In dimethylformamide, 0.05 mol of p-phenylenediamine, 0.3 mol ofp-nitroiodobenzene, 0.12 mol of anhydrous potassium carbonate, andcopper powder were added and refluxed with stirring for 4 days. Afterthe reaction was completed, the reaction mixture was filtered, and thefiltered product was thoroughly washed with dimethylformamide, water andacetone, followed by drying. Thus, 0.040 mol of reddish browntetrakis(p-nitrophenyl)-p-phenylenediamine was obtained.

In an autoclave, 12 parts of the compound thus obtained was addedtogether with 50 parts of dimethylformamide and 0.5 part ofpalladium-carbon hydrogenated catalyst, and hydrogen gas was appliedthereto at 5.0 kg/cm², followed by stirring at 90° C. to 100° C. untilthe absorption of hydrogen ceased.

After the reaction was completed, the reaction fluid was filtered, andthe filtered product was washed with dimethylformamide and then waspoured into 200 parts of ice water. After stirring for a while, theprecipitate was collected by filtration. This precipitate wasrecrystallized using an ethanol-dimethylformamide mixed solvent, to give8 parts of tetrakis(p-aminophenyl)-p-phenylenediamine. Its purity wasmeasured by high-speed liquid chromatography to reveal that it was99.0%.

As a result of NMR (d₆ -DMSO) analysis subsequently carried out,absorption of amino groups corresponding to 8 hydrogen atoms wasobserved at δ3.36 ppm, and a broad doublet absorption of an aromaticring corresponding to 20 hydrogen atoms, at δ6.40 to 6.50 ppm.

Synthesis of Compound No.(I)-(A)-(1)

Together with 12 parts of dimethylformamide, 0.5 part of anhydroussodium hydrogencarbonate and 4.0 parts of 2,2,2-trifluoroethyl iodide, 2parts of the amino compound described above was heated and stirred at100° C. to 130° C. After the reaction was carried out for 36 hours, thereaction fluid was poured into 80 parts of ice water, followed byextraction with ethyl acetate. The extract was dried and then purifiedusing silica gel columns to givetetrakis[bis-(2-trifluoroethyl)aminophenyl]phenylenediamine, which wasobtained in an amount of 1.6 parts. The compound thus obtained wassubjected to infrared absorption analysis to confirm the extinction ofabsorption according to NH stretching vibration of amino groups.

In 18 parts of acetone, 1 part of this compound was dispersed, to whichan equimolar amount of silver perchlorate was added with stirring. Afterthe reaction was carried out at room temperature for 1 hour, the silverdeposited was separated by filtration, and the filtrate was diluted withisopropyl ether. The dilute solution was left to stand, and greencrystals deposited were collected by filtration to give the endcompound, which was obtained in an amount of 0.6 part.

    ______________________________________                                        C.sub.46 H.sub.36 N.sub.6 F.sub.24 ClO.sub.4 (molecular weight:               1,228.28)                                                                              C          H       N                                                 ______________________________________                                        Calculated:                                                                              44.98%       2.95%   6.84%                                         Found:     44.96%       2.94%   6.83%                                         ______________________________________                                    

The compound thus obtained was subjected to measurement of itsabsorption maximum wavelength, using a spectrophotometer (trade name:U-3410; manufactured by Hitachi Ltd.) to reveal that it was a compoundwith a region of large absorption in the infrared region at 1,260 nm and960 nm each.

Synthesis of Compound No.(II)-(A)-(8)

In 25 parts of acetone, 1 part of thetetrakis[bis-(2-trifluoroethyl)aminophenyl]phenylenediamine as used inthe synthesis of compound No.(I)-(A)-(1) was dispersed, and to thedispersion 2-fold mole of silver hexafluoroantimonate was added withstirring. After the reaction was carried out at room temperature for 1hour, the silver deposited was separated by filtration, and the filtratewas diluted with isopropyl ether. Dark blue crystals deposited werecollected by filtration to give 60 parts of the compound. This compoundwas an infrared-absorptive compound having a maximum absorption at 1,178nm.

    ______________________________________                                        C.sub.46 H.sub.36 N.sub.6 F.sub.36 Sb.sub.2 (molecular weight: 1,600.35)               C          H       N                                                 ______________________________________                                        Calculated:                                                                              34.52%       2.27%   5.25%                                         Found:     34.50%       2.25%   5.23%                                         ______________________________________                                    

Synthesis Example 2

While applying ammonia gas at 42.0 kg/cm² in an autoclave, 0.1 mol of9,10-dibromoanthracene was stirred at 190° to 200° C. to give 0.08 molof 9,10-diaminoanthracene.

In dimethylformamide, 0.05 mol of 9,10-diaminoanthracene, 0.35 mol ofp-nitroiodobenzene, 0.14 mol of anhydrous potassium carbonate, andcopper powder were added and refluxed with stirring for 4 days. Afterthe reaction was completed, the reaction mixture was filtered, and thefiltered product was thoroughly washed with dimethylformamide, water andacetone, followed by drying. Thus, 0.043 mol of browntetrakis(p-nitrophenyl)-9,10-diaminoanthracene was obtained.

In an autoclave, 13 parts of the compound thus obtained was addedtogether with 60 parts of dimethylformamide and 0.5 part ofpalladium-carbon hydrogenated catalyst, and hydrogen gas was appliedthereto at 5.0 kg/cm², followed by stirring at 90° C. to 100° C. untilthe absorption of hydrogen ceased.

After the reaction was completed, the reaction fluid was filtered, andthe filtered product was washed with dimethylformamide and then waspoured into 250 parts of ice water. After stirring for a while, theprecipitate was collected by filtration. This precipitate wasrecrystallized using an ethanol-dimethylformamide mixed solvent, to give7 parts of tetrakis(p-aminophenyl)-9,10-diaminoanthracene. Its puritywas measured by high-speed liquid chromatography to reveal that it was98.8%.

As a result of NMR (d₆ -DMSO) analysis of this compound, absorption ofamino groups corresponding to 8 hydrogen atoms was observed at δ3.37ppm, and a broad absorption of an aromatic ring corresponding to 24hydrogen atoms, at δ6.38 to 6.51 ppm.

Synthesis of Compound No.(III)-(5)

Together with 13 parts of dimethylformamide, 6 part of anhydrous sodiumhydrogencarbonate and 5.0 parts of propyl bromide, 2 parts of the aminocompound described above was heated and stirred at 100° C. to 130° C.After the reaction was carried out for 36 hours, the reaction fluid waspoured into 90 parts of ice water, followed by extraction with ethylacetate. The extract was dried and then purified using silica gelcolumns to give tetrakis(p-propylaminophenyl)-9,10-diaminoanthracene,which was obtained in an amount of 1.6 parts. The compound thus obtainedwas subjected to infrared absorption analysis to confirm the extinctionof absorption according to NH stretching vibration of amino groups.

In 19 parts of acetone, 1 part of this compound was dispersed, to whichan equimolar amount of silver perchlorate was added with stirring. Afterthe reaction was carried out at room temperature for 1 hour, the silverdeposited was separated by filtration, and the filtrate was diluted withisopropyl ether. The dilute solution was left to stand, and crystalsdeposited were collected by filtration to give the end compound, whichwas obtained in an amount of 0.7 part.

The compound thus obtained was a compound with a region of largeabsorption in the infrared region at 1,250 nm and 956 nm each.

    ______________________________________                                        C.sub.62 H.sub.80 N.sub.6 ClO.sub.4 (molecular weight: 1,008.80)                       C          H       N                                                 ______________________________________                                        Calculated:                                                                              73.82%       8.00%   8.33%                                         Found:     73.83%       7.98%   8.30%                                         ______________________________________                                    

Synthesis of Compound No.(IV)-(28)

In 22 parts of acetone, 1 part of thetetrakis(p-propylaminophenyl)-9,10-diaminoanthracene as used in thesynthesis of compound No.(III)-(5) was dispersed, and to the dispersion2-fold mole of silver hexafluoroantimonate was added with stirring.After the reaction was carried out at room temperature for 1 hour, thesilver deposited was separated by filtration, and the filtrate wasdiluted with isopropyl ether. Crystals deposited were collected byfiltration to give 0.58 part of the compound. This compound Was aninfrared-absorptive compound having a maximum absorption at 1,178 nm.

    ______________________________________                                        C.sub.62 H.sub.80 N.sub.6 Sb.sub.2 F.sub.12 (molecular weight: 1,380.87)               C          H       N                                                 ______________________________________                                        Calculated:                                                                              53.93%       5.84%   6.09%                                         Found:     53.90%       5.82%   6.07%                                         ______________________________________                                    

Synthesis Example 3

In dimethylformamide, 0.05 mol of 2,7-diamino-9-fluorenone, 0.3 mol ofp-nitroiodobenzene, 0.12 mol of anhydrous potassium carbonate, andcopper powder were added and refluxed with stirring for 4 days. Afterthe reaction was completed, the reaction mixture was filtered, and thefiltered product was thoroughly washed with dimethylformamide, water andacetone, followed by drying. Thus, 0.038 mol of reddish browntetrakis(p-nitrophenyl)-2,7-diamino-9-fluorenone was obtained.

In an autoclave, 12 parts of the compound thus obtained was addedtogether with 50 parts of dimethylformamide and 0.5 part ofpalladium-carbon hydrogenated catalyst, and hydrogen gas was appliedthereto at 5.0 kg/cm², followed by stirring at 90° C. to 100° C. untilthe absorption of hydrogen ceased.

After the reaction was completed, the reaction fluid was filtered, andthe filtered product was washed with dimethylformamide and then waspoured into 200 parts of ice water. After stirring for a while, theprecipitate was collected by filtration. This precipitate wasrecrystallized using an ethanol-dimethylformamide mixed solvent, to give7 parts of tetrakis(p-aminophenyl)-2,7-diamino-9-fluorenone. Its puritywas measured by high-speed liquid chromatography to reveal that it was98.9%.

As a result of NMR (d₆ -DMSO) analysis subsequently carried out,absorption of amino groups corresponding to 8 hydrogen atoms wasobserved at δ3.36 ppm, and a broad absorption of an aromatic ringcorresponding to 22 hydrogen atoms, at δ6.38 to 6.51 ppm.

Synthesis of Compound No.(V)-A-(5)

Together with 12 parts of dimethylformamide, 0.5 part of anhydroussodium hydrogencarbonate and 5.0 parts of n-propyl bromide, 2 parts ofthe amino compound described above was heated and stirred at 100° C. to130° C. After the reaction was carried out for 36 hours, the reactionfluid was poured into 90 parts of ice water, followed by extraction withethyl acetate. The extract was dried and then purified using silica gelcolumns to give tetrakis(p-propylaminophenyl)-2,7-diamino-9-fluorenone,which was obtained in an amount of 1.7 parts. The compound thus obtainedwas subjected to infrared absorption analysis to confirm the extinctionof absorption according to NH stretching vibration of amino groups.

In 19 parts of acetone, 1 part of this compound was dispersed, to whichan equimolar amount of silver perchlorate was added with stirring. Afterthe reaction was carried out at room temperature for 1 hour, the silverdeposited was separated by filtration, and the filtrate was diluted withisopropyl ether. The dilute solution was left to stand, and crystalsdeposited were collected by filtration to give the end compound, whichwas obtained in an amount of 0.7 part.

The compound thus obtained was a compound with a region of largeabsorption in the infrared region at 1,255 nm and 960 nm each.

    ______________________________________                                        C.sub.61 H.sub.78 N.sub.6 ClO.sub.5 (molecular weight: 1,010.78)                       C          H       N                                                 ______________________________________                                        Calculated:                                                                              72.49%       7.78%   8.31%                                         Found:     72.47%       7.76%   8.28%                                         ______________________________________                                    

Synthesis of Compound No.(VI)-A-(22)

In 22 parts of acetone, 1 part of thetetrakis(p-propylaminophenyl)-2,7-diamino-9-fluorenone as used in thesynthesis of compound No.(V)-A-(5) was dispersed, end to the dispersion2-fold mole of silver hexafluoroantimonate was added with stirring.After the reaction was carried out at room temperature for 1 hour, thesilver deposited was separated by filtration, and the filtrate wasdiluted with isopropyl ether. Crystals deposited were collected byfiltration to give 0.56 part of the compound. This compound was aninfrared-absorptive compound having a maximum absorption at 1,185 nm.

    ______________________________________                                        C.sub.61 H.sub.78 N.sub.6 Sb.sub.2 F.sub.12 (molecular weight: 1,382.83)               C          H       N                                                 ______________________________________                                        Calculated:                                                                              52.98%       5.69%   6.08%                                         Found:     52.97%       5.67%   6.06%                                         ______________________________________                                    

Examples in which the infrared-absorptive compound of the presentinvention is applied in optical recording mediums will be describedbelow.

Example 101

On a polycarbonate (hereinafter "PC")substrate of a wallet size (arectangle of 54 mm long and 85 mm broad) and 0.4 mm thick, pregrooves of3 μm in width and 3,000 Å in depth were provided in a pitch of 12 μm byhot pressing, in parallel to the longitudinal direction of thesubstrate, and a solution prepared by dissolving in 97 parts by weightof diacetone alcohol 3 parts by weight of a mixture (weight ratio:75:25) comprised of a polymethine dye (trade name: IR-820; availablefrom Nippon Kayaku Co., Ltd.) and the infrared-absorptive compound No.(I)-(A)(4) described above was coated thereon by bar coating, followedby drying to form a recording layer of 900 Å in thickness.

To this recording layer, a PC protective substrate of the same walletsize as the PC substrate and 0.3 mm thick was laminated, interposing anacrylate-ethylene copolymer dry film between them, and thencontact-bonded by hot rolling. Thus, an optical card of bonded laminatestructure was produced.

The optical card thus obtained was irradiated with a semiconductor laserbeam of an oscillation wavelength of 830 nm using an optical cardrecording-reproducing apparatus (manufactured by Canon Inc.), throughthe 0.4 mm thick PC substrate, and the reflectance from the recordinglayer at that time was measured. Subsequently, through the 0.4 mm thickPC substrate, information was written in the recording tracks formedbetween pregrooves, at a recording power of 3.5 mW and a recording pulseof 80 μsec, and then reproduced at a reproducing power of 0.4 mW tomeasure its contrast ratio [(A-B)/A, wherein A represents a signalintensity at an unrecorded area and B represents a signal intensity at arecorded area].

The reflectance and contrast ratio at this time are regarded as initialvalues.

Next, this optical card was left to stand in an environment of 85° C.high temperature for 1,000 hours, and thereafter its reflectance andcontrast ratio were measured (environmental storage stability).

The optical card of Example 101, anew produced and in which theinformation was recorded in entirely the same way, was also irradiatedwith 1 kW/m² xenon lamp light for 100 hours to measure its reflectanceand contrast ratio (light-resistance stability). In order to alsoevaluate heat resistance of this optical card, the rate of change of thecontrast ratio obtained in the environmental storage stability test withrespect to the initial contrast ratio (ΔCont) was determined.

Results obtained are shown in Table 101.

Comparative Example 101

An optical card was produced in the same manner as in Example 101 exceptthat the infrared-absorptive compound No. (I)-(A)-(4) used therein wasreplaced with an aminium salt compound represented by the followingformula. Evaluation was also similarly made.

Results obtained are shown in Table 101. ##STR1316##

Comparative Example 102

An optical card was produced in the same manner as in Example 101 exceptthat the infrared-absorptive compound No. (I)-(A)-(4) used therein wasremoved. Evaluation was also similarly made.

Results obtained are shown in Table 101.

                                      TABLE 101                                   __________________________________________________________________________           (1)        (2)        (3)                                                     Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           ΔCont                                  (%)   ratio                                                                              (%)   ratio                                                                              (%)   ratio                                                                              (%)                                   __________________________________________________________________________    Example:                                                                             14.7  0.64 13.2  0.57 12.9  0.56 10.9                                  101                                                                           Comparative                                                                   Example:                                                                      101    14.7  0.64 12.1  0.51 12.4  0.55 20.0                                  102    15.0  0.65 13.3  0.58 10.7  0.48 10.8                                  __________________________________________________________________________     (1): Initial stage                                                            (2): Environmental storage stability test (85° C., dry, after 1,00     hours)                                                                        (3): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Examples 102 & 103

Optical cards were each produced in the same manner as in Example 101except that the combination of the polymethine dye and theinfrared-absorptive compound of the present invention as used thereinwas changed to the combination of an organic dye and aninfrared-absorptive compound as shown in Table 102 below. Evaluation onthe optical cards thus obtained was similarly made.

Results obtained are shown in Table 103.

                                      TABLE 102                                   __________________________________________________________________________                                              Infrared-                                                                     absorptive                          Example                                                                             Organic dye                         comp. No.                                                                            Wt. ratio                    __________________________________________________________________________    102                                                                                  ##STR1317##                        [II]-(C)-(1)                                                                         60:40                        103                                                                                  ##STR1318##                        [I] -(A)-(35)                                                                        85:15                        __________________________________________________________________________

Comparative Example 103

An optical card was produced in the same manner as in Example 102 exceptthat the infrared-absorptive compound No. (II)-(C)-(1) used therein wasreplaced with a diimonium salt compound of the following structure.Evaluation was also similarly made.

Results obtained are shown in Table 103. ##STR1319##

Comparative Example 104

An optical card was produced in the same manner as in Example 103 exceptthat the infrared-absorptive compound No. (I)-(A)-(35) used therein wasreplaced with an aminium salt compound of the following structure.Evaluation was also similarly made.

Results obtained are shown in Table 103. ##STR1320##

                                      TABLE 103                                   __________________________________________________________________________           (1)        (2)        (3)                                                     Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           ΔCont                                  (%)   ratio                                                                              (%)   ratio                                                                              (%)   ratio                                                                              (%)                                   __________________________________________________________________________    Example:                                                                      102    14.5  0.60 11.9  0.49 12.5  0.52 18.3                                  103    14.9  0.65 12.5  0.55 12.2  0.53 15.4                                  Comparative                                                                   Example:                                                                      103    14.5  0.60 10.2  0.41 12.6  0.52 31.7                                  104    14.9  0.65 10.5  0.45 12.3  0.53 30.8                                  __________________________________________________________________________     (1): Initial stage                                                            (2): Environmental storage stability test (85° C., dry, after 1,00     hours)                                                                        (3): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Examples 104 to 108

Optical cards were each produced in the same manner as in Example 101except that the combination of the polymethine dye and theinfrared-absorptive compound of the present invention as used thereinwas changed to the combination of an organic dye and aninfrared-absorptive compound as shown in Table 104 below. Evaluation onthe optical cards thus obtained was similarly made.

Results obtained are shown in Table 105.

                                      TABLE 104                                   __________________________________________________________________________                                                Infrared-                                                                     absorptive                        Example                                                                            Organic dye                            comp. No.                                                                             Wt.                       __________________________________________________________________________                                                        ratio                     104                                                                                 ##STR1321##                           [I]-(A)-(18)                                                                          80:20                     105                                                                                 ##STR1322##                           [II]-(B)-(6)                                                                          70:30                     106                                                                                 ##STR1323##                           [I]-(D)-(13)                                                                          90:10                     107                                                                                 ##STR1324##                           [I]-(E)-(5)                                                                           75:25                     108                                                                                 ##STR1325##                           [I]-(D)-(3) [II]-(D)-(10)                                                             75:15:10                  __________________________________________________________________________

Comparative Examples 106 & 107

Optical cards were produced in the same manner as in Example 101 exceptthat the infrared-absorptive compounds used in Examples 102 and 108,i.e., No. (II)-(C)-(1) and Nos. (I)-(D)-(3) and (II)-(D)-(10),respectively, were removed. Evaluation was also similarly made.

Results obtained are shown in Table 105.

                                      TABLE 105                                   __________________________________________________________________________           (1)        (2)        (3)                                                     Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                          (%)   ratio                                                                              (%)   ratio                                                                              (%)   ratio                                      __________________________________________________________________________    Example:                                                                      104    15.3  0.66 13.2 0.55  12.7  0.54                                       105    14.9  0.62 12.7 0.53  12.5  0.53                                       106    15.4  0.65 12.9 0.55  12.5  0.53                                       107    15.5  0.67 12.7 0.54  13.0  0.56                                       108    15.5  0.66 12.87                                                                              0.54  13.0  0.55                                       Comparative                                                                   Example:                                                                      106    16.3  0.69 9.8  0.41  6.8   0.19                                       107    16.0  0.68 9.3  0.38  9.6   0.37                                       __________________________________________________________________________     (1): Initial stage                                                            (2): Environmental storage stability test (85° C., dry, after 1,00     hours)                                                                        (3): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Example 109

On a PC substrate of 130 mm diameter and 1.2 mm thick, having beenprovided with a 0.6 82 m wide and 1.6 μm pitch spiral pregroove byinjection molding, a solution prepared by dissolving in 95 parts byweight of diacetone alcohol 5 parts by weight of a mixture comprised ofa polymethine organic dye (trade name: IR-820; available from NipponKayaku Co., Ltd.) and the infrared-absorptive compound No. (I)-(A)-(9)was coated by spin coating to form a recording layer of 950 Å inthickness. Subsequently, this substrate with the recording layer waslaminated to a PC protective substrate of 130 mm diameter and 1.2 mmthick using an ultraviolet-curable adhesive, interposing 0.3 mm spacersprovided at the inner boundary edge and outer boundary edge of theformer substrate. Thus an optical disk of air-sandwich structure wasobtained.

Reflectance to light with a wavelength of 830 nm, of the recording layerof the optical disk thus obtained was measured using a spectrophotometer(trade name: U-3400; manufactured by Hitachi Lid,.). The resulting valueis regarded as an initial reflectance.

Next, this optical disk was fitted to a turn table. While the turn tablewas driven by a motor and rotated at 1,800 rpm, information was writtenin the recording layer from the substrate side at a recording power of 8mW and a recording frequency of 3 MHz using a semiconductor layer of anoscillation wavelength of 830 nm. The recorded information wasreproduced at a read-out power of 0.8 mW, and its reproduction wave formwas spectrally analyzed (a scanning filter; bandwidth: 30 KHz) tomeasure C/N ratio (carrier-noise ratio). The resulting value is regardedas an initial C/N ratio.

Next, on this optical disk, the portions recorded under the aboveconditions were repeatedly read out 10⁵ times to measure C/N ratio afterthat.

The optical disk of Example 109, anew produced in entirely the same wayas described above, was made ready and information was recorded underthe same conditions as the above recording conditions. Thereafter, thisoptical disk was left to stand in an environment of 85° C. for 1,000hours, and thereafter the reflectance of its recording layer to lightwith a wavelength of 830 nm and the C/N ratio of recorded informationwere measured in the same manner as described above (environmentalstorage stability).

The optical disk of Example 109, further anew produced in entirely thesame way as described above, was made ready and information was recordedunder the same conditions as the above recording conditions. Thereafter,this optical disk was irradiated with 1 kW/m² xenon lamp light for 100hours to measure its reflectance and C/N ratio. In order to alsoevaluate heat resistance of this optical disk, the rate of change of theC/N ratio obtained in the environmental storage stability test withrespect to the initial contrast ratio (ΔC/N) was determined.

Results obtained are shown in Table 106.

Comparative Example 108

An optical disk was produced in the same manner as in Example 109 exceptthat the infrared-absorptive compound used therein was replaced with anaminium salt compound represented by the following structural formula.Evaluation was also similarly made.

Results obtained are shown in Table 106. ##STR1326##

Example 110

On a polymethyl methacrylate (hereinafter "PMMA") substrate of 130 mmdiameter and 1.2 mm thick, a pregroove layer of 30 μm thick was providedby the 2P process (photo-polymer process) using an epoxy-acrylate typeultraviolet-curable resin. On this substrate, a solution prepared bydissolving in 98 parts by weight of 1,2-dichloroethane 2 parts by weightof a mixture (weight ratio: 85:15) comprised of an organic dye havingthe following structure and the infrared-absorptive compound No.(II)-(A)-(27) was coated by spin coating, followed by drying to form arecording layer with a thickness of 850 Å. The subsequent procedure ofExample 109 was repeated to produce an optical disk.

On the optical disk thus produced, measurement and evaluation were madein the same manner as in Example 109.

Results obtained are shown in Table 106. ##STR1327##

Comparative Example 109

An optical disk was produced in the same manner as in Example 110 exceptthat the infrared-absorptive compound (II)-(A)-(27) used therein wasreplaced with a diimonium salt compound having the following structure.Evaluation was also similarly made.

Results obtained are shown in Table 106.

                                      TABLE 106                                   __________________________________________________________________________     ##STR1328##                                                                          (1)        (2) (3)        (4)                                                 Reflectance                                                                          C/N C/N Reflectance                                                                          C/N Reflectance                                                                          C/N ΔC/N                               (%)    (dB)                                                                              (dB)                                                                              (%)    (dB)                                                                              (%)    (dB)                                                                              (%)                              __________________________________________________________________________    Example:                                                                              25.7   56  54  22.4   48  23.1   51  14.3                             109                                                                           Comparative                                                                           25.6   56  54  19.2   42  23.0   51  25.0                             Example:                                                                      108                                                                           Example:                                                                              25.9   58  54  22.0   49  21.8   49  15.5                             110                                                                           Comparative                                                                           25.8   58  54  18.5   42  21.9   50  27.5                             Example:                                                                      109                                                                           __________________________________________________________________________     (1): Initial stage                                                            (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85° C., dry, after 1,000         hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Examples 111 to 114

Optical disks were each produced in the same manner as in Example 109except that the combination of the organic dye and theinfrared-absorptive compound as used therein was changed to thecombination as shown in Table 107 below. Evaluation was similarly made.

Results obtained are shown in Table 108.

Comparative Examples 110 & 111

Optical disks were produced in the same manner as in Examples 111 and114, respectively, except that the infrared-absorptive compounds No.(II)-(C)-(9) and No. (I)-(A)-(31) used therein were removed. Evaluationwas similarly made.

Results obtained are shown in Table 108.

                                      TABLE 107                                   __________________________________________________________________________                                                     Infrared-                                                                     absorptive                   Example                                                                              Organic dye                               comp. No.                                                                             Wt.                  __________________________________________________________________________                                                             ratio                111                                                                                   ##STR1329##                              [II]-(C)-(9)                                                                          70:30                112                                                                                   ##STR1330##                              [I]-(B)-(3)                                                                           85:15                113                                                                                   ##STR1331##                              [II]-(D)-(12)                                                                         90:10                114                                                                                   ##STR1332##                              [I]-(A)-(31)                                                                          75:25                __________________________________________________________________________

                                      TABLE 108                                   __________________________________________________________________________           (1)       (2) (3)       (4)                                                   Reflectance                                                                         C/N C/N Reflectance                                                                         C/N Reflectance                                                                         C/N                                             (%)   (dB)                                                                              (dB)                                                                              (%)   (dB)                                                                              (%)   (dB)                                     __________________________________________________________________________    Example:                                                                      111    25.4  55  52  21.6  47  22.6  49                                       112    25.9  57  52  22.1  48  22.3  49                                       113    26.0  57  54  21.3  46  21.6  48                                       114    26.3  59  55  22.4  50  22.9  52                                       Comparative                                                                   Example:                                                                      110    27.2  61  46  16.3  36  16.9  37                                       111    30.1  60  38  15.4  29  15.1  30                                       __________________________________________________________________________     (1): Initial stage                                                            (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85° C., dry, after 1,000         hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Example 115

An optical disk was produced in the same manner as in Example 110 exceptthat the combination of the organic dye and the infrared-absorptivecompound as used therein was changed to the combination as shown inTable 109 below. Evaluation was similarly made.

Results obtained are shown in Table 110.

Examples 116 & 117

A solution prepared by mixing in 95 parts by weight of diacetone alcohol4 parts by weight of mixture comprised of the combination of an organicdye and an infrared-absorptive compound as shown in Table 109 below and1 part by weight of nitrocellulose resin (O'hares Lacquer, availablefrom Daicel Chemical Industries, Ltd.) was coated on a pregroovedpolycarbonate substrate of 130 mm diameter and 1.2 mm thick, prepared inthe same manner as in Example 109, followed by drying to form arecording layer with a thickness of 950 Å. The subsequent procedure ofExample 109 was repeated to produce optical disks.

On the optical disks thus produced, measurement was made in the samemanner as in Example 109.

Results obtained are shown in Table 110.

                                      TABLE 109                                   __________________________________________________________________________                                               Infrared-                                                                     absorptive                         Example                                                                             Organic dye                          comp. No.                                                                             Wt. ratio                  __________________________________________________________________________    115                                                                                  ##STR1333##                         [I]-(A)-(37)                                                                          80:20                      116                                                                                  ##STR1334##                         [I] -(E)-(13)                                                                         65:35                      117                                                                                  ##STR1335##                         [II]-(A)-(16)                                                                         70:30                      __________________________________________________________________________

                                      TABLE 110                                   __________________________________________________________________________    (1)            (2) (3)       (4)                                                   Reflectance                                                                         C/N C/N Reflectance                                                                         C/N Reflectance                                                                         C/N                                        Example                                                                            (%)   (dB)                                                                              (dB)                                                                              (%)   (dB)                                                                              (%)   (dB)                                       __________________________________________________________________________    115  26.0  59  55  22.6  51  22.1  51                                         116  24.7  53  51  21.5  46  21.7  47                                         117  24.8  52  49  21.3  45  21.6  46                                         __________________________________________________________________________     (1): Initial stage                                                            (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85° C., dry, after 1,000         hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Example 201

On a PC substrate prepared in the same manner as in Example 101, asolution prepared by dissolving in 97 parts by weight of diacetonealcohol 3 parts by weight of a mixture (weight ratio: 75:25) comprisedof a polymethine dye (trade name: IR-820; available from Nippon KayakuCo., Ltd.) and the infrared-absorptive compound No. (III)-(14)previously set out was coated by bar coating, followed by drying to forma recording layer of 850 Å in thickness.

To this recording layer, a PC protective substrate of the same walletsize as the PC substrate and 0.3 mm thick was laminated, interposing anacrylate-ethylene copolymer dry film between them, and thencontact-bonded by hot rolling. Thus, an optical card of bonded laminatestructure was produced.

On the optical card thus obtained, the initial reflectance and contrastratio were measured in the same manner as in Example 101. Theenvironmental storage stability and the light-resistance stability werealso similarly evaluated.

Results Obtained are shown in Table 201.

Comparative Example 201

An optical card was produced in the same manner as in Example 201 exceptthat the infrared-absorptive compound No. (III)-(14) used therein wasreplaced with an aminium salt compound represented by the followingformula. Evaluation was also similarly made.

Results obtained are shown in Table 201.

                                      TABLE 201                                   __________________________________________________________________________     ##STR1336##                                                                          (1)          (2)          (3)                                                 Reflectance                                                                          Contrast                                                                            Reflectance                                                                          Contrast                                                                            Reflectance                                                                          Contrast                                                                            ΔCont                            (%)    ratio (%)    ratio (%)    ratio (%)                            __________________________________________________________________________    Example:                                                                              14.6   0.63  13.1   0.56  12.8   0.55  11.1                           201                                                                           Comparative                                                                           14.7   0.64  11.7   0.50  13.0   0.56  21.9                           Example:                                                                      201                                                                           __________________________________________________________________________     (1): Initial stage                                                            (2): Environmental storage stability test (85° C., dry, after 1,00     hours)                                                                        (3): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours

Examples 202 & 203

Optical cards were each produced in the same manner as in Example 201except that the combination of the organic dye and theinfrared-absorptive compound as used therein was changed to thecombination as shown in Table 202 below. Evaluation was similarly made.

Results obtained are shown in Table 203.

                                      TABLE 202                                   __________________________________________________________________________                                           Infrared-                                                                     absorptive                             Example                                                                             Organic dye                      comp. No.                                                                            Wt. ratio                       __________________________________________________________________________    202                                                                                  ##STR1337##                     [III]-(18)                                                                           80:20                           203                                                                                  ##STR1338##                     [IV]-(14)                                                                            70:30                           __________________________________________________________________________

Comparative Examples 202 & 203

Optical cards were produced in the same manner as in Examples 202 and203, respectively, except that the infrared-absorptive compounds usedtherein were respectively replaced with an aminium salt compound and adiimonium compound represented by the following formulas. Evaluation wasalso similarly made.

Results obtained are shown in Table 203. ##STR1339##

                                      TABLE 203                                   __________________________________________________________________________           (1)        (2)        (3)                                                     Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           ΔCont                                  (%)   ratio                                                                              (%)   ratio                                                                              (%)   ratio                                                                              (%)                                   __________________________________________________________________________    Example:                                                                             15.1  0.65 13.1  0.54 12.8  0.53 16.9                                  202                                                                           Comparative                                                                          15.2  0.65 11.2  0.46 12.9  0.54 29.2                                  Example:                                                                      202                                                                           Example:                                                                             14.8  0.61 12.5  0.52 12.5  0.51 14.8                                  203                                                                           Comparative                                                                          14.8  0.61 10.3  0.42 12.7  0.52 31.1                                  Example:                                                                      203                                                                           __________________________________________________________________________     (1): Initial stage                                                            (2): Environmental storage stability test (85° C., dry, after 1,00     hours)                                                                        (3): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Examples 204 to 208

Optical cards were each produced in the same manner as in Example 201except that the combination of the organic dye and theinfrared-absorptive compound as used therein was changed to thecombination as shown in Table 204 below. Evaluation was similarly made.

Results obtained are shown in Table 205.

Comparative Examples 204 & 205

Optical cards were produced in the same manner as in Examples 203 and206, respectively, except that the infrared-absorptive compounds usedtherein were removed. Evaluation was also similarly made.

Results obtained are shown in Table 205.

                                      TABLE 204                                   __________________________________________________________________________                                                 Infrared-                                                                     absorptive                       Example                                                                             Organic dye                            comp. No.                                                                            Wt.                       __________________________________________________________________________                                                        ratio                     204                                                                                  ##STR1340##                           [III]-(10)                                                                           60:40                     205                                                                                  ##STR1341##                           [IV]-(25)                                                                            90:10                     206                                                                                  ##STR1342##                           [III]-(20)                                                                           75:25                     207                                                                                  ##STR1343##                           [III]-(14)                                                                           85:15                     208                                                                                  ##STR1344##                           [III]-(27)/ [IV]-(27)                                                                75:15:10                  __________________________________________________________________________

                                      TABLE 205                                   __________________________________________________________________________           (1)        (2)        (3)                                                     Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                          (%)   ratio                                                                              (%)   ratio                                                                              (%)   ratio                                      __________________________________________________________________________    Example:                                                                      204    14.6  0.59 11.9 0.48  12.6  0.53                                       205    15.4  0.66 12.7 0.55  12.4  0.52                                       206    5.6   0.68 12.6 0.53  13.1  0.56                                       207    4.8   0.65 12.5 0.56  12.3  0.54                                       208    5.6   0.66 12.8 0.55  13.1  0.55                                       Comparative                                                                   Example:                                                                      204    17.9  0.70 9.5  0.39  6.7   0.20                                       205    20.5  0.69 9.3  0.37  *     *                                          __________________________________________________________________________     (1): Initial stage                                                            (2): Environmental storage stability test (85° C., dry, after 1,00     hours)                                                                        (3): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours     *Unmeasurable                                                            

Example 209

On the optical disk substrate as prepared in Example 109, a solutionprepared by dissolving in 95 parts by weight of diacetone alcohol 5parts by weight of a mixture (weight ratio: 80:20) comprised of apolymethine organic dye (trade name: IR-820; available from. NipponKayaku Co., Ltd.) and the infrared-absorptive compound No. (III)-(35)was coated by spin coating to form a recording layer of 900 Å inthickness. Subsequently, this substrate with the recording layer waslaminated to a PC protective substrate using an ultraviolet-curableadhesive, interposing 0.3 mm spacers provided at the inner boundary edgeand outer boundary edge of the former substrate. Thus an optical disk ofair-sandwich structure was obtained.

On the optical disk thus obtained, evaluation was made in the samemanner as in Example 109.

Results obtained are shown in Table 206.

Comparative Example 206

An optical disk was produced in the same manner as in Example 209 exceptthat the infrared-absorptive compound used therein was replaced with anaminium salt compound having the following structure. Evaluation wasalso similarly made.

Results obtained are shown in Table 206. ##STR1345##

Example 210

On the optical disk substrate as prepared in Example 110, a solutionprepared by dissolving in 98 parts by weight of 1,2-dichloroethane 2parts by weight of a mixture (weight Patio: 63:35) comprised of anorganic dye having the following structure and the infrared-absorptivecompound No. (III)-(25) was coated by spin coating, followed by dryingto form a recording layer with a thickness of 850 Å. The subsequentprocedure of Example 209 was repeated to produce an optical disk.

On the optical disk thus produced, measurement and evaluation were madein the same manner as in Example 110.

Results obtained are shown in Table 206. ##STR1346##

Comparative Example 207

An optical disk was produced in the same manner as in Example 210 exceptthat the infrared-absorptive compound used therein was replaced with anaminium salt compound having the following structure. Evaluation wasalso similarly made.

Results obtained are shown in Table 206.

                                      TABLE 206                                   __________________________________________________________________________     ##STR1347##                                                                          (1)        (2) (3)        (4)                                                 Reflectance                                                                          C/N C/N Reflectance                                                                          C/N Reflectance                                                                          C/N ΔC/N                               (%)    (dB)                                                                              (dB)                                                                              (%)    (dB)                                                                              (%)    (dB)                                                                              (%)                              __________________________________________________________________________    Example:                                                                              25.6   56  53  22.3   49  23.2   50  12.5                             209                                                                           Comparative                                                                           25.7   56  53  19.5   43  23.3   51  23.2                             Example:                                                                      206                                                                           Example:                                                                              24.5   53  50  21.3   45  21.6   45  15.1                             210                                                                           Comparative                                                                           24.6   53  51  17.8   38  21.6   45  28.3                             Example:                                                                      207                                                                           __________________________________________________________________________     (1): Initial stage                                                            (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85° C., dry, after 1,000         hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Examples 211 to 214

Optical disks were each produced in the same manner as in Example 209except that the combination of the organic dye and theinfrared-absorptive compound as used therein was changed to thecombination as shown in Table 207 below. Evaluation was similarly made.

Results obtained are shown in Table 208.

Comparative Examples 208 to 210

Optical disks were produced in the same manner as in Example 209 exceptthat the infrared-absorptive compounds used in Examples 209, 213 and214, respectively, were removed. Evaluation was similarly made.

Results obtained are shown in Table 208.

                                      TABLE 207                                   __________________________________________________________________________                                                     Infrared-                                                                     absorptive                   Example                                                                              Organic dye                               comp. No.                                                                             Wt.                  __________________________________________________________________________                                                             ratio                211                                                                                   ##STR1348##                              [IV]-(3)                                                                              70:30                212                                                                                   ##STR1349##                              [III]-(32)                                                                            85:15                213                                                                                   ##STR1350##                              [IV]-(4)                                                                              90:10                214                                                                                   ##STR1351##                              [III]-(28)                                                                            75:25                __________________________________________________________________________

                                      TABLE 208                                   __________________________________________________________________________           (1)       (2) (3)       (4)                                                   Reflectance                                                                         C/N C/N Reflectance                                                                         C/N Reflectance                                                                         C/N                                             (%)   (dB)                                                                              (dB)                                                                              (%)   (dB)                                                                              (%)   (dB)                                     __________________________________________________________________________    Example:                                                                      211    25.3  54  51  21.5  47  22.4  48                                       212    25.8  56  51  22.0  47  22.2  48                                       213    25.7  55  53  21.1  45  21.0  44                                       214    26.2  58  54  22.3  49  22.7  51                                       Comparative                                                                   Example:                                                                      208    27.0  57  51  22.4  50  19.5  40                                       209    26.5  58  50  15.8  37  16.0  32                                       210    30.2  59  39  14.8  28  14.7  28                                       __________________________________________________________________________     (1): Initial stage                                                            (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85° C., dry, after 1,000         hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Example 215

An optical disk was produced in the same manner as in Example 210 exceptthat the combination of the organic dye and the infrared-absorptivecompound as used therein was changed to the combination as shown inTable 209 below. Evaluation was similarly made.

Results obtained are shown in Table 210.

Examples 216 & 217

A solution prepared by mixing in 95 parts by weight of diacetone alcohol4 parts by weight of a mixture comprised of the combination of anorganic dye and an infrared-absorptive compound as shown in Table 209below and 1 part by weight of nitrocellulose resin (O'hares Lacquer,available from Daicel Chemical Industries, Ltd.) was coated on apregrooved polycarbonate substrate of 130 mm diameter and 1.2 mm thick,prepared in the same manner as in Example 109, followed by drying toform a recording layer with a thickness of 1,000 Å. The subsequentprocedure of Example 109 was repeated to produce optical disks.

On the optical disks thus produced, measurement was made in the samemanner as in Example 209.

Results obtained are shown in Table 210.

                                      TABLE 209                                   __________________________________________________________________________                                                     Infrared-absorptive                                                                     Wt.                Example                                                                            Organic dye                                 comp. No. ratio              __________________________________________________________________________    215                                                                                 ##STR1352##                                [IV]-(10) 85:15              216                                                                                 ##STR1353##                                [III]-(31)                                                                              80:20              217                                                                                 ##STR1354##                                [IV]-(5)  70:30              __________________________________________________________________________

                                      TABLE 210                                   __________________________________________________________________________    (1)            (2) (3)       (4)                                                   Reflectance                                                                         C/N C/N Reflectance                                                                         C/N Reflectance                                                                         C/N                                        Example                                                                            (%)   (dB)                                                                              (dB)                                                                              (%)   (dB)                                                                              (%)   (dB)                                       __________________________________________________________________________    215  25.8  57  53  21.8  48  21.7  48                                         216  25.8  58  53  22.5  50  22.0  51                                         217  24.7  51  49  21.3  44  21.4  45                                         __________________________________________________________________________     (1): Initial stage                                                            (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85° C., dry, after 1,000         hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Example 301

On a pregrooved wallet-size PC substrate prepared in the same manner asin Example 101, a solution prepared by dissolving in 97 parts by weightof diacetone alcohol 3 parts by weight of a mixture (weight ratio:75:25) comprised of a polymethine dye (trade name: IR-820; availablefrom Nippon Kayaku Co., Ltd.) and the infrared-absorptive compound No.(V)-(D)-(16) was coated by bar coating, followed by drying to form arecording layer of 900 Å in thickness.

To this recording layer, a PC protective substrate of the same walletsize as the PC substrate and 0.3 mm thick was laminated, interposing anacrylate-ethylene copolymer dry film between them, and thencontact-bonded by hot rolling. Thus, an optical card of bonded laminatestructure was produced.

On the optical card thus obtained, the initial reflectance and contrastratio were measured in the same manner as in Example 101. Theenvironmental storage stability and the light-resistance stability werealso similarly evaluated.

Results obtained are shown in Table 301.

Comparative Example 301

An optical card was produced in the same manner as in Example 301 exceptthat the infrared-absorptive compound No. (V)-(D)-(16) used therein wasreplaced with an aminium salt compound represented by the followingformula. Evaluation was similarly made.

Results obtained are shown in Table 301. ##STR1355##

Example 302

An optical card was produced in the same manner as in Example 301 exceptthat the combination of the organic dye and the infrared-absorptivecompound as used therein was changed to the combination as shown below.Evaluation was similarly made.

Results obtained are shown in Table 301.

    __________________________________________________________________________                                                    Infrared-absorptive                                                                     Wt.                 Example                                                                            Organic dye                                comp. No. ratio               __________________________________________________________________________    302                                                                                 ##STR1356##                               [VI]-(B)-(12)                                                                           80:20               __________________________________________________________________________

Comparative Example 302

An optical card was produced in the same manner as in Example 302 exceptthat the infrared-absorptive compound No. (VI)-(B)-(12) used therein wasreplaced with a diimonium salt compound represented by the followingformula. Evaluation was similarly made.

Results obtained are shown in Table 301.

                                      TABLE 301                                   __________________________________________________________________________     ##STR1357##                                                                          (1)         (2)          (3)                                                  Reflectance                                                                         Contrast                                                                            Reflectance                                                                          Contrast                                                                            Reflectance                                                                          Contrast                                                                            ΔCont                             (%)   ratio (%)    ratio (%)    ratio (%)                             __________________________________________________________________________    Example:                                                                              14.9  0.64  13.2   0.57  12.4   0.59  11.0                            301                                                                           Comparative                                                                           14.9  0.64  11.5   0.49  12.3   0.58  23.4                            Example:                                                                      301                                                                           Example:                                                                              16.1  0.65  13.6   0.55  12.0   0.53  15.4                            302                                                                           Comparative                                                                           16.0  0.64  11.2   0.45  12.0   0.52  29.7                            Example:                                                                      302                                                                           __________________________________________________________________________     (1): Initial stage                                                            (2): Environmental storage stability test (85° C., dry, after 1,00     hours)                                                                        (3): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Examples 303 to 305

Optical cards were each produced in the same manner as in Example 301except that the combination of the organic dye and theinfrared-absorptive compound as used therein was changed to thecombination as shown in Table 302 below. Evaluation was similarly made.

Results obtained are shown in Table 303.

                                      TABLE 302                                   __________________________________________________________________________                                            Infrared-absorptive                                                                       Wt.                       Example                                                                            Organic dye                        comp. No.   ratio                     __________________________________________________________________________    303                                                                                 ##STR1358##                       [VI]-(A)-10 85:15                     304                                                                                 ##STR1359##                       [V]-(C)-(8) 80:20                     305                                                                                 ##STR1360##                       [V]-(B)-(7)/[V]-(A)-(22)                                                                  85:10:5                   __________________________________________________________________________

Comparative Example 303

An optical card was produced in the same manner as in Example 302 exceptthat the infrared-absorptive compounds used therein was removed.Evaluation was also similarly made.

Results obtained are shown in Table 303.

                                      TABLE 303                                   __________________________________________________________________________           (1)        (2)        (3)                                                     Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                                                           Reflectance                                                                         Contrast                                          (%)   ratio                                                                              (%)   ratio                                                                              (%)   ratio                                      __________________________________________________________________________    Example:                                                                      303    15.3  0.61 13.4 0.54  12.3  0.55                                       304    15.2  0.63 13.2 0.56  12.7  0.56                                       305    15.8  0.61 13.3 0.53  12.3  0.54                                       Comparative                                                                          16.2  0.66 13.5 0.54  9.3   0.43                                       Example:                                                                      303                                                                           __________________________________________________________________________     (1): Initial stage                                                            (2): Environmental storage stability test (85° C., dry, after 1,00     hours)                                                                        (3): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Example 306

On the optical disk substrate prepared in the same manner as in Example110, a solution prepared by dissolving in 1,2-dichloroethane a mixture(weight ratio: 80:20) comprised of a polymethine organic dye (tradename: IR-820; available from Nippon Kayaku Co., Ltd.) and theinfrared-absorptive compound No. (V)-(A)-(5) previously described wascoated by spin coating, followed by drying to form a recording layerwith a thickness of 900 Å. The subsequent procedure of Example 109 wasrepeated to produce an optical disk.

On the optical disk thus obtained, evaluation was made in the samemanner as in Example 110.

Results obtained are shown in Table 304.

Comparative Example 304

An optical disk was produced in the same manner as in Example 306 exceptthat the infrared-absorptive compound No. (V)-(A)-(5) used therein wasreplaced with an aminium salt compound having the following structure.Evaluation was similarly made.

Results obtained are shown in Table 304. ##STR1361##

Example 307

An optical disk was produced in the same manner as in Example 306 exceptthat the combination of the organic dye and the infrared-absorptivecompound as used therein was changed to the combination as shown below.Evaluation was similarly made. Results obtained are shown in Table 304.

    __________________________________________________________________________                                        Infrared-absorptive                                                                     Wt.                             Example                                                                            Organic dye                    comp. No. ratio                           __________________________________________________________________________    307                                                                                 ##STR1362##                   [VI]-(C)-(2)                                                                            80:20                           __________________________________________________________________________

Comparative Example 305

An optical disk was produced in the same manner as in Example 307 exceptthat the infrared-absorptive compound No. (VI)-(C)-(2) used therein wasreplaced with a diimonium salt compound having the following structure.Evaluation was similarly made.

Results obtained are shown in Table 304.

                                      TABLE 304                                   __________________________________________________________________________     ##STR1363##                                                                         (1)      (2)                                                                              (3)      (4)                                                      Reflectance                                                                         C/N                                                                              C/N                                                                              Reflectance                                                                         C/N                                                                              Reflectance                                                                         C/N                                                                              ΔC/N                                      (%)   (dB)                                                                             (dB)                                                                             (%)   (dB)                                                                             (%)   (dB)                                                                             (%)                                      __________________________________________________________________________    Example:                                                                             24.8  57 55 21.6  50 22.7  54 12.3                                     306                                                                           Comparative                                                                          24.8  57 55 18.7  43 22.6  53 24.6                                     Example:                                                                      304                                                                           Example:                                                                             25.3  53 50 21.5  45 20.5  49 15.1                                     307                                                                           Comparative                                                                          25.4  53 50 17.9  39 20.6  49 26.4                                     Example:                                                                      305                                                                           __________________________________________________________________________      (1): Initial stage                                                           (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85°C., dry, after 1,000          hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Examples 308 to 313

Optical disks were each produced in the same manner as in Example 306except that the combination of the organic dye and theinfrared-absorptive compound as used therein was changed to thecombination as shown in Tables 305 and 305 below, Evaluation wassimilarly made.

Results obtained are shown in Table 307.

                                      TABLE 305                                   __________________________________________________________________________                                             Infrared-absorptive                                                                     Wt.                        Example                                                                            Organic dye                         comp. No. ratio                      __________________________________________________________________________    308                                                                                 ##STR1364##                        [V]-(B)-(8)                                                                             85:15                      309                                                                                 ##STR1365##                        [V]-(A)-(22)                                                                            90:10                      310                                                                                 ##STR1366##                        [V]-(D)-(10)                                                                            70:30                      __________________________________________________________________________

                                      TABLE 306                                   __________________________________________________________________________                                         Infrared-absorption                                                                        Wt.                         Example                                                                            Organic dye                     comp. No.    ratio                       __________________________________________________________________________    311                                                                                 ##STR1367##                    [V]-(C)-(14) 75:25                       312                                                                                 ##STR1368##                    [VI]-(D)-(13)                                                                              85:15                       313                                                                                 ##STR1369##                    [V]-(B)-(10)/[VI]-(B)-(10)                                                                 80:10/10                    __________________________________________________________________________

Comparative Examples 306 & 307

Optical disks were produced in the same manner as in Examples 308 and311, respectively, except that the infrared-absorptive compounds usedtherein were removed. Evaluation was also similarly made.

Results obtained are shown in Table 307.

                                      TABLE 307                                   __________________________________________________________________________           (1)       (2) (3)       (4)                                                   Reflectance                                                                         C/N C/N Reflectance                                                                         C/N Reflectance                                                                         C/N                                             (%)   (dB)                                                                              (dB)                                                                              (%)   (dB)                                                                              (%)   (dB)                                     __________________________________________________________________________    Example:                                                                      308    27.2  56  54  23.1  48  23.6  52                                       309    27.4  55  52  23.8  48  24.2  51                                       310    22.5  51  50  26.7  42  22.4  48                                       311    26.3  55  54  22.2  46  22.3  51                                       312    25.7  53  52  21.7  46  21.6  50                                       313    24.9  54  50  21.8  46  21.5  50                                       Comparative                                                                   Example:                                                                      306    27.8  57  39  23.3  48  14.2  36                                       307    26.5  56  38  22.4  47  13.8  33                                       __________________________________________________________________________     (1): Initial stage                                                            (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85° C., dry, after 1,000         hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Examples 314 & 317

A solution prepared by mixing in 95 parts by weight of diacetone alcohol4 parts by weight of a mixture comprised of the combination of anorganic dye and an infrared-absorptive compound as shown in Table 3.8below and 1 part by weight of nitrocellulose resin (O'hares Lacquer,available from Daicel Chemical Industries, Ltd.) was coated on apregrooved polycarbonate substrate of 130 mm diameter and 1.2 mm thick,prepared in the same manner as in Example 109, followed by drying toform a recording layer with a thickness of 950 Å. The subsequentprocedure of Example 109 was repeated to produce optical disks.

On the optical disks thus produced, measurement was made in the samemanner as in Example 306.

Results obtained are shown in Table 309.

                                      TABLE 308                                   __________________________________________________________________________                                        Infrared-absorption                                                                     Wt.                             Example                                                                            Organic dye                    comp. No. ratio                           __________________________________________________________________________    314                                                                                 ##STR1370##                   [VI]-(A)-(16)                                                                           70:30                           315                                                                                 ##STR1371##                   [V]-(D)-(7)                                                                             85:15                           316                                                                                 ##STR1372##                   [VI]-(C)-(9)                                                                            75:25                           317                                                                                 ##STR1373##                   [V]-(B)-(12)                                                                            80:20                           __________________________________________________________________________

                                      TABLE 309                                   __________________________________________________________________________    (1)            (2) (3)       (4)                                                   Reflectance                                                                         C/N C/N Reflectance                                                                         C/N Reflectance                                                                         C/N                                        Example                                                                            (%)   (dB)                                                                              (dB)                                                                              (%)   (dB)                                                                              (%)   (dB)                                       __________________________________________________________________________    314  26.4  53  51  22.0  44  22.6  48                                         315  25.9  54  52  22.5  47  22.3  49                                         316  26.0  51  48  22.1  44  23.1  49                                         317  25.5  53  51  21.7  45  22.6  49                                         __________________________________________________________________________     (1): Initial stage                                                            (2): Repeated reproduction (after 10.sup.5 times)                             (3): Environmental storage stability (85° C., dry, after 1,000         hours)                                                                        (4): Lightresistance stability (xenon lamp, 1 kW/m.sup.2, after 100 hours                                                                              

Example 401

A solution was prepared by dissolving in 97 parts by weight of diacetonealcohol 3 parts by weight of a mixture (weight ratio: 75:25) comprisedof the organic dye of Example 104 and the infrared-absorptive compoundNo. (I)-(A)-(18).

Meanwhile, 200 sheets of pregrooved wallet-size PC substrates as used inExample 104 were prepared. On the substrates, the above solution wascontinuously coated by roll coating, followed by drying to form arecording layer with a thickness of 1,000 Å on each substrate.Thereafter, using each substrate with the recording layer formedthereon, 200 cards were produced in the same manner as in Example 101.

Then, optical cards produced using substrates on which the recordinglayers were formed on the 1st coating, 10th coating, 50th coating, 100thcoating and 200th coating (hereinafter called optical cards No. 1, No.10, No. 50, No. 100 and No. 200, respectively) were picked up, and eachwas set on an optical card recording-reproducing apparatus. While theoptical card was driven in the direction following the pregrooves, lightwas made incident from the PC substrate side on the recording layerformed on recording tracks between the grooves, using a semiconductorlaser of an oscillation wavelength of 830 nm, to record informationunder the following recording conditions.

Recording conditions:

Spot size: 3 μm in diameter

Recording power: 10 mW

Recording frequency: 150 kHz

Transport speed: 480 mm/sec.

Subsequently, beams of the semiconductor laser, whose power was reducedto 0.3 mW, were made to scan the recording tracks along whichinformation had been recorded, to reproduce the information. Theresulting reproducing wave form was spectrally analyzed to measure noiselevel and C/N ratio of each optical card.

Results obtained are shown in Table 401.

Examples 402 to 405

Two hundred (200) optical cards were produced in the same manner as inExample 401 except that the infrared-absorptive compound No.(I)-(A)-(18) used therein was replaced with No. (I)-(A)-(35), No.(I)-(A)-(37), No. (III)-(14) or No.. (V)-(D)-(7). Evaluation was alsosimilarly made.

Results obtained are shown in Table 401.

Comparative Example 401

An optical card was produced in the same manner as in Example 401 exceptthat the infrared-absorptive compound No. (I)-(A)-(18) used therein wasreplaced with the infrared-absorptive compound used in ComparativeExample 101. Its noise level and C/N ratio were measured in the samemanner as in Example 401.

Results obtained ape shown in Table 401.

Reference Example 401

Two hundred (200) optical cards were produced in the same manner as inExample 401 except that the infrared-absorptive compound No.(I)-(A)-(18) used therein was replaced with No. (I)-(A)-(15). Evaluationwas also similarly made.

Results obtained are shown in Table 401.

                  TABLE 401                                                       ______________________________________                                        C/N ratio (dB); In ( ): noise level                                                  No.1   No.10   No.50     No.100                                                                              No.200                                         card   card    card      card  card                                    ______________________________________                                        Example:                                                                      401      49       49      49      49    49                                             (-68)    (-68)   (-68)   (-68) (-68)                                 402      49       49      49      49    49                                             (-68)    (-68)   (-68)   (-68) (-68)                                 403      50       50      50      50    50                                             (-68)    (-68)   (-68)   (-68) (-68)                                 404      49       49      49      49    49                                             (-68)    (-68)   (-68)   (-68) (-68)                                 405      48       48      48      48    48                                             (-67)    (-67)   (-67)   (-67) (-67)                                 Comparative                                                                            48       48      47      45    44                                    Example: (-67)    (-67)   (-66)   (-64) (-62)                                 401                                                                           Synthesis                                                                              49       49      48      47    46                                    Example: (-68)    (-68)   (-67)   (-66) (-65)                                 401                                                                           ______________________________________                                    

In Comparative Example 401, the nose level increased and the C/N ratiodecreased with an increase in the coating number. This is presumed to bedue to an insufficient solvent solubility of the infrared-absorptivecompound used in Comparative Example 401, which has easily causeddeposition of solid matter, e.g., fine crystals, because of a slightchange in concentration of the coating solution, caused when coated on anumber of substrates, and this had caused the noise. On the other hand,it can be considered that the infrared-absorptive compound of thepresent invention has so high a solvent solubility and so hardly causethe deposition of crystals even because of some change in concentrationin the coating step that no crystals can be included in the recordinglayer and optical recording mediums with a low noise level can beobtained.

What is claimed is:
 1. An optical recording medium comprising arecording layer formed on a substrate containing an infrared-absorptivecompound represented by the following formula (I) or (II) ##STR1374##wherein R₀ to R₇ each represent (a) a hydrogen atom or a monovalentorganic residual group, at least one of R₀ to R₇ being a monovalentorganic residual group having a fluorine atom, or (b) a group of atomsnecessary for at least one of combinations R₀ and R₁, R₂ and R₃, R₄ andR₅ and R₆ and R₇ to form together with a nitrogen atom a substituted5-membered ring having a fluorine atom, a substituted 6-membered ringhaving a fluorine atom or a substituted 7-membered ring having afluorine atom, other combinations each being a hydrogen atom or amonovalent organic residual group; X.sup.⊖ represents an anionicresidual group; in formula (I), "A" represents ##STR1375## and informula (II), "B" represents ##STR1376## wherein n represents an integerof 1 or
 2. 2. The optical recording medium according to claim 1, whereinsaid monovalent organic residual group is a substituted alkyl grouphaving a fluorine atom, a substituted alkenyl group having a fluorineatom, a substituted aralkyl group having a fluorine atom, or asubstituted aryl group having a fluorine atom.
 3. The optical recordingmedium according to claim 1, wherein said 5-membered ring is apyrrolidine ring.
 4. The optical recording medium according to claim 1,wherein said 6-membered ring is a piperidine ring or atetrahydropyridine ring.
 5. The optical recording medium according toclaim 1, wherein said 7-membered ring is a cyclohexylamine ringrepresented by the following formula VII. ##STR1377##
 6. An opticalrecording medium comprising a recording layer containing aninfrared-absorptive compound represented by the formula (III) or (IV)##STR1378## wherein R'₁ to R'₁₆ each represent a hydrogen atom or amonovalent organic residual group, or a group of atoms necessary for anycombination of R'_(q) and R'_(q+1) to form a substituted orunsubstituted 5-membered ring, a substituted or unsubstituted 6-memberedring or a substituted or unsubstituted 7-membered ring, wherein q is 1,3, 5, 7, 9, 11 or 13; and X.sup.⊖ represents an anionic residual group.7. An optical recording medium comprising a recording layer containingan infrared-absorptive compound represented by the following formula (V)or (VI) ##STR1379## wherein Z represents ##STR1380## R"₁ to R"₉ eachrepresent a hydrogen atom or a monovalent organic residual group, or agroup of atoms necessary for any combination of R"_(r) and R"_(r+1) toform a substituted or unsubstituted 5-membered ring, a substituted orunsubstituted 6-membered ring or a substituted or unsubstituted7-membered ring, wherein r is 1, 3, 5 or 7; and X.sup.⊖ represents ananionic residual group.